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{{Short description|Naturally produced monosaccharide}}
{{Use dmy dates|date=June 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Chembox
| verifiedrevid = 818842877
| Name = {{sm|d}}-Glucose
| ImageFile =
| ImageClass = skin-invert-image
| ImageCaption = [[Skeletal formula]] of {{sm|d}}-glucose
| pronounce = {{IPAc-en|ˈ|ɡ|l|uː|k|oʊ|z}}, {{IPAc-en||ɡ|l|uː|k|oʊ|s}}
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| ImageSize2 = 120
| ImageCaption2 = [[Haworth projection]] of α-{{sm|d}}-glucopyranose
| ImageClass2 = skin-invert-image
| ImageFile3 = D-glucose chain (Fischer).svg
| ImageSize3 = 100
| ImageCaption3 = [[Fischer projection]] of {{sm|d}}-glucose
| ImageClass3 = skin-invert-image
| PIN = PINs are not identified for natural products.
| SystematicName = {{clear}}
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* (3''R'',4''S'',5''S'',6''R'')-6-(hydroxymethyl)oxane-2,3,4,5-tetrol <small>'''(cyclic form)'''</small>
| OtherNames = Blood sugars<br>Dextrose<br>Corn sugar<br>{{sm|d}}-Glucose<br>Grape sugar
| IUPACName = Allowed trivial names:<ref>[https://iupac.qmul.ac.uk/2carb/02.html Nomenclature of Carbohydrates (Recommendations 1996) {{!}} 2-Carb-2] {{Webarchive|url=https://web.archive.org/web/20230827082825/https://iupac.qmul.ac.uk/2carb/02.html |date=
* HEXAN1-AL 2,3,4,5,6 HEXOL
* ᴅ-''gluco''-Hexose
| Section1 = {{Chembox Identifiers
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}}
| Section2 = {{Chembox Properties
| C=6 | H=12 | O=6
| MolarMassUnit = g/mol
| Appearance = White powder
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| Density = 1.54 g/cm<sup>3</sup>
| Solubility = 909 g/L ({{convert|25|C}})
| Dipole =
| MagSus = −101.5×10<sup>−6</sup> cm<sup>3</sup>/mol
}}
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| DeltaHf = −1271 kJ/mol<ref>{{citation | last1 = Ponomarev | first1 = V. V. | last2 = Migarskaya | first2 = L. B. | title = Heats of combustion of some amino-acids | journal = Russ. J. Phys. Chem. (Engl. Transl.) | year = 1960 | volume = 34 | pages = 1182–83}}</ref>
| HHV = {{cvt|2805|kJ/mol|kcal/mol}}
| Entropy = 209.2 J/(K·mol)<ref name="Boerio-Goates 1991 403–9">{{citation | last = Boerio-Goates | first = Juliana | title = Heat-capacity measurements and thermodynamic functions of crystalline α-D-glucose at temperatures from 10K to 340K | journal = J. Chem. Thermodyn. | year = 1991 | volume = 23 | issue = 5 | pages = 403–09 | doi = 10.1016/S0021-9614(05)80128-4| bibcode = 1991JChTh..23..403B }}</ref>
| HeatCapacity = 218.6 J/(K·mol)<ref name="Boerio-Goates 1991 403–9"/>
}}
| Section6 = {{Chembox Pharmacology
| Pharmacology_ref =
| ATCCode_prefix = B05
| ATCCode_suffix = CX01
| ATC_Supplemental = {{ATC|V04|CA02}}, {{ATC|V06|DC01}}
| ATCvet =
}}▼
| Licence_EU =
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| INN_EMA =
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| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_AU_comment =
| Dependence_liability =
| AdminRoutes =
| Bioavail =
| ProteinBound =
| Metabolism =
| Metabolites =
| OnsetOfAction =
| HalfLife =
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| Excretion =
▲ }}
| Section7 = {{Chembox Hazards
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0865.htm ICSC 08655]
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}}
}}
'''Glucose''' is a [[sugar]] with the [[Chemical formula#Molecular formula|molecular formula]] {{chem2|auto=1|C6H12O6}}. Glucose is overall the most abundant [[monosaccharide]],<ref name="DombKost1998">{{Cite book |url=https://books.google.com/books?id=iLjhl6AvfIsC&pg=PA275 |isbn=978-1-4200-4936-7 |page=275|title=Handbook of Biodegradable Polymers |last1=Domb |first1=Abraham J. |last2=Kost |first2=Joseph |last3=Wiseman |first3=David |date=1998-02-04 |publisher=CRC Press }}</ref> a subcategory of [[carbohydrate]]s. Glucose is mainly made by [[plants]] and most [[algae]] during [[photosynthesis]] from water and carbon dioxide, using energy from sunlight, where it is used to make [[cellulose]] in [[cell wall]]s, the most abundant carbohydrate in the world or, ATP([[Adenosine triphosphate|Adenosine Triphosphate]]) which is used by the cell as energy.<ref name="froms">{{cite web | url=https://drugs.ncats.io/drug/IY9XDZ35W2 | title=NCATS Inxight Drugs — DEXTROSE, UNSPECIFIED FORM | access-date=2024-03-18 | archive-date=2023-12-11 | archive-url=https://web.archive.org/web/20231211224631/https://drugs.ncats.io/drug/IY9XDZ35W2 | url-status=live }}</ref><ref>{{cite book |last1=Kamide |first1=Kenji |title=Cellulose products and Cellulose Derivatives: Molecular Characterization and its Applications |date=2005 |publisher=Elsevier |location=Amsterdam |isbn=978-0-08-045444-3 |page=1 |edition=1st |url=https://books.google.com/books?id=28Vx9OkEtQcC&pg=PA1 |access-date=13 May 2021}}</ref><ref name="r2"/>▼
▲'''Glucose''' is a [[sugar]] with the [[Chemical formula#Molecular formula|molecular formula]] {{chem2|auto=1|C6H12O6}}.
In [[energy metabolism]], glucose is the most important source of energy in all [[organism]]s. Glucose for metabolism is stored as a [[polymer]], in plants mainly as [[starch]] and [[amylopectin]], and in animals as [[glycogen]]. Glucose circulates in the blood of animals as [[blood sugar]].<ref name="froms"/><ref name="r2"/> The naturally occurring form of glucose is {{sm|d}}-glucose, while its [[Stereoisomerism|stereoisomer]] [[L-glucose|{{sm|l}}-glucose]] is produced synthetically in comparatively small amounts and is less biologically active.<ref name="r2">{{Cite web |date=2019-10-07 |title=L-glucose |url=https://www.biologyonline.com/dictionary/l-glucose |access-date=2022-05-06 |website=Biology Articles, Tutorials & Dictionary Online |language=en-US |archive-date=2022-05-25 |archive-url=https://web.archive.org/web/20220525135220/https://www.biologyonline.com/dictionary/l-glucose |url-status=live }}</ref> Glucose is a monosaccharide containing six carbon atoms and an [[aldehyde]] group, and is therefore an [[aldohexose]]. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Glucose is naturally occurring and is found in its free state in fruits and other parts of plants. In animals, glucose is released from the breakdown of glycogen in a process known as [[glycogenolysis]].▼
▲In [[energy metabolism]], glucose is the most important source of energy in all [[organism]]s. Glucose for metabolism is stored as a [[polymer]], in plants mainly as [[
Glucose, as [[intravenous sugar solution]], is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> It is also on the list in combination with [[sodium chloride]] (table salt).<ref name="WHO21st" />▼
▲Glucose, as [[intravenous sugar solution]], is on the [[
The name glucose is derived from [[Ancient Greek]] {{lang|grc|γλεῦκος}} ({{transliteration|grc|gleûkos}}, "wine, must"), from {{lang|grc|γλυκύς}} ({{transliteration|grc|glykýs}}, "sweet").<ref>{{cite web |url=http://www.etymonline.com/index.php?term=glucose |title=Online Etymology Dictionary |website=Etymonline.com |access-date=2016-11-25 |url-status=live |archive-url= https://web.archive.org/web/20161126065057/http://www.etymonline.com/index.php?term=glucose |archive-date=2016-11-26 }}</ref><ref>Thénard, Gay-Lussac, Biot, and Dumas (1838) [http://gallica.bnf.fr/ark:/12148/bpt6k29662/f106.langEN "Rapport sur un mémoire de M. Péligiot, intitulé: Recherches sur la nature et les propriétés chimiques des sucres"]. {{webarchive|url= https://web.archive.org/web/20151206043449/http://gallica.bnf.fr/ark:/12148/bpt6k29662/f106.langEN |date=2015-12-06 }} (Report on a memoir of Mr. Péligiot, titled: Investigations on the nature and chemical properties of sugars), ''Comptes rendus'', '''7''' : 106–113. [http://gallica.bnf.fr/ark:/12148/bpt6k29662/f109.langEN From page 109]. {{webarchive|url=https://web.archive.org/web/20151206050123/http://gallica.bnf.fr/ark:/12148/bpt6k29662/f109.langEN |date=2015-12-06 }}: "Il résulte des comparaisons faites par M. Péligot, que le sucre de raisin, celui d'amidon, celui de diabètes et celui de miel ont parfaitement la même composition et les mêmes propriétés, et constituent un seul corps que nous proposons d'appeler {{em|Glucose}} (1). ... (1) γλευχος, moût, vin doux." It follows from the comparisons made by Mr. Péligot, that the sugar from grapes, that from starch, that from diabetes and that from honey have exactly the same composition and the same properties, and constitute a single substance that we propose to call ''glucose'' (1) ... (1) γλευχος, must, sweet wine.</ref> The suffix "[[-ose]]" is a chemical classifier denoting a sugar.▼
▲The name glucose is derived from [[Ancient Greek]] {{lang|grc|γλεῦκος}} ({{transliteration|grc|gleûkos}}
==History==
Glucose was first isolated from [[raisin]]s in 1747 by the German chemist [[Andreas Sigismund Marggraf|Andreas Marggraf]].<ref name="Encyclopedia of Food and Health">{{cite book|title=Encyclopedia of Food and Health|date=2015|publisher=Academic Press|isbn=978-0-12-384953-3|page=239|url=https://books.google.com/books?id=O-t9BAAAQBAJ&pg=RA2-PA239|language=en|url-status=live|archive-url=https://web.archive.org/web/20180223145046/https://books.google.com/books?id=O-t9BAAAQBAJ&pg=RA2-PA239|archive-date=
Since glucose is a basic necessity of many organisms, a correct understanding of its [[chemical]] makeup and structure contributed greatly to a general advancement in [[organic chemistry]]. This understanding occurred largely as a result of the investigations of [[Hermann Emil Fischer|Emil Fischer]], a German chemist who received the 1902 [[Nobel Prize in Chemistry]] for his findings.<ref>{{citation | title = Emil Fischer | url = http://nobelprize.org/nobel_prizes/chemistry/laureates/1902/fischer-bio.html | publisher = Nobel Foundation | access-date = 2 September 2009
For the discovery of the metabolism of glucose [[Otto Meyerhof]] received the [[Nobel Prize in Physiology or Medicine]] in 1922.<ref>[https://www.nobelprize.org/nobel_prizes/medicine/laureates/1922/meyerhof-facts.html "Otto Meyerhof - Facts - NobelPrize.org"] {{Webarchive|url=https://web.archive.org/web/20180715011915/https://www.nobelprize.org/nobel_prizes/medicine/laureates/1922/meyerhof-facts.html |date=
== Chemical and physical properties ==
Glucose forms white or colorless solids that are highly [[
With six carbon atoms, it is classed as a [[hexose]], a subcategory of the [[monosaccharide]]s. {{sm|d}}-Glucose is one of the sixteen [[aldohexose]] [[stereoisomer]]s. The {{sm|d}}-[[isomer]], {{sm|d}}-glucose, also known as dextrose, occurs widely in nature, but the {{sm|l}}-isomer, [[L-glucose|{{sm|l}}-glucose]], does not. Glucose can be obtained by [[hydrolysis]] of carbohydrates such as milk sugar ([[lactose]]), cane sugar (sucrose), [[maltose]], [[cellulose]], [[glycogen]], etc. Dextrose is commonly commercially manufactured from [[Starch|starches]], such as [[corn starch]] in the US and Japan, from potato and wheat starch in Europe, and from [[tapioca starch]] in tropical areas.<ref>{{Citation|last=Yebra-Biurrun|first=M.C.|title=Sweeteners|date=2005|encyclopedia=Encyclopedia of Analytical Science|pages=562–572|publisher=Elsevier|language=en|doi=10.1016/b0-12-369397-7/00610-5|isbn=978-0-12-369397-6}}</ref> The manufacturing process uses hydrolysis via pressurized steaming at controlled [[pH]] in a jet followed by further enzymatic depolymerization.<ref>"glucose." The Columbia Encyclopedia, 6th ed.. 2015. Encyclopedia.com. 17
The term ''dextrose'' is often used in a clinical (related to patient's health status) or nutritional context (related to dietary intake, such as food labels or dietary guidelines), while "glucose" is used in a biological or physiological context (chemical processes and molecular interactions),<ref>{{Cite web |url=https://diabetesjournals.org/care/article/28/4/981/23717/Potentially-Important-Contribution-of-Dextrose |title=Potentially Important Contribution of Dextrose Used as Diluent to Hyperglycemia in Hospitalized Patients | Diabetes Care | American Diabetes Association |access-date=
''Dextrose monohydrate'' is the hydrated form of D-glucose, meaning that it is a glucose molecule with an additional water molecule attached.<ref name="chem"/> Its chemical formula is {{chem2|C6H12O6}} · {{chem2|H2O}}.<ref name="chem"/><ref name="api110617">{{cite web | url=https://www.cdek.liu.edu/api/110617/ | title=API | glucose monohydrate | access-date=
''Anhydrous dextrose'', on the other hand, is glucose that does not have any water molecules attached to it.<ref name="diff"/> <ref name="ahn1">{{Cite web|url=https://www.chembk.com/en/chem/Dextrose%20anhydrous|title=Dextrose anhydrous|access-date=
Anhydrous dextrose has the chemical formula {{chem2|C6H12O6}}, without any water molecule attached which is the same as glucose.<ref name="chem"/> Anhydrous dextrose on open air tends to absorb moisture and transform to the monohydrate, and it is more expensive to produce.<ref name="diff"/> Anhydrous dextrose (anhydrous D-glucose) has increased stability and increased shelf life,<ref name="a2"/> has medical applications, such as in oral [[glucose tolerance test]]
Whereas molecular weight (molar mass) for D-glucose monohydrate is 198.17 g/mol,<ref>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/22814120 | title=Dextrose Monohydrate | access-date=
In terms of chemical structure, glucose is a
===Structure and nomenclature===
Glucose is
{{See also|Mutarotation}}▼
▲Glucose is not present in solid form as a [[monohydrate]] with a closed [[pyran]] ring (α-glucopyranose monohydrate, sometimes known less precisely by dextrose hydrate). In aqueous solution, on the other hand, it is an open-chain to a small extent and is present predominantly as α- or β-[[pyranose]], which interconvert. From aqueous solutions, the three known forms can be crystallized: α-glucopyranose, β-glucopyranose and α-glucopyranose monohydrate.<ref name="Ullmann">{{Cite book |doi=10.1002/14356007.a12_457.pub2 |chapter=Glucose and Glucose-Containing Syrups |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2006 |last1=Schenck |first1=Fred W. |isbn=978-3-527-30673-2}}</ref> Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of [[oligosaccharide]]s such as [[raffinose]] and of [[polysaccharide]]s such as [[starch]], [[amylopectin]], [[glycogen]], and [[cellulose]].<ref name="r2"/><ref name="pf"/> The [[glass transition temperature]] of glucose is {{cvt|31|C}} and the Gordon–Taylor constant (an experimentally determined constant for the prediction of the glass transition temperature for different mass fractions of a mixture of two substances)<ref name="pf">Patrick F. Fox: ''Advanced Dairy Chemistry Volume 3: Lactose, water, salts and vitamins'', Springer, 1992. Volume 3, {{ISBN|9780412630200}}. p. 316.</ref> is 4.5.<ref name="Caballero 1 76">Benjamin Caballero, Paul Finglas, Fidel Toldrá: ''Encyclopedia of Food and Health''. Academic Press (2016). {{ISBN|9780123849533}}, Volume 1, p. 76.</ref>
{| class="wikitable centered"
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! colspan="2"| [[Haworth projection]]
|- class="background color2"
| align="center" rowspan="2" | [[File:D-Glucose Keilstrich.svg|100px|class=skin-invert-image]]
| align="center" | [[File:Alpha-D-Glucofuranose.svg|120px|class=skin-invert-image]]{{pb}}α-{{sm|d}}-glucofuranose
| align="center" | [[File:Beta-D-Glucofuranose.svg|120px|class=skin-invert-image]]{{pb}}β-{{sm|d}}-glucofuranose
|- class="background color2"
| align="center" | [[File:Alpha-D-Glucopyranose.svg|100px|class=skin-invert-image]]{{pb}}α-{{sm|d}}-glucopyranose
| align="center" | [[File:Beta-D-Glucopyranose.svg|100px|class=skin-invert-image]]{{pb}}β-{{sm|d}}-glucopyranose
|- class="background color5"
! colspan="3"| α-{{sm|d}}-Glucopyranose in (1) [[Fischer projection|Tollens/Fischer]] (2) Haworth projection (3) chair conformation (4) Mills projection
|- class="background color2"
| align="center" colspan="3" | [[File:Alpha glucose views.svg|500px|class=skin-invert-image]]
|}
===Open-chain form===
[[Image:Glucose Fisher to Haworth.gif|thumb|class=skin-invert-image|Glucose can exist in both a straight-chain and ring form.]]
A open-chain form of glucose makes up less than 0.02% of the glucose molecules in an aqueous solution at equilibrium.<ref>{{Cite web |date=
===Cyclic forms===
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The ring-closing reaction can give two products, denoted "α-" and "β-". When a glucopyranose molecule is drawn in the [[Haworth projection]], the designation "α-" means that the hydroxyl group attached to C-1 and the {{chem2|\sCH2OH}} group at C-5 lies on opposite sides of the ring's plane (a[[cis–trans isomerism|'' trans'']] arrangement), while "β-" means that they are on the same side of the plane (a[[cis–trans isomerism|'' cis'']] arrangement). Therefore, the open-chain isomer {{small|D}}-glucose gives rise to four distinct cyclic isomers: α-{{small|D}}-glucopyranose, β-{{small|D}}-glucopyranose, α-{{small|D}}-glucofuranose, and β-{{small|D}}-glucofuranose. These five structures exist in equilibrium and interconvert, and the interconversion is much more rapid with acid [[catalysis]].
[[File:Alpha-D-glucose and beta-D-glucose acid-catalyzed mechanism.svg|centre|500px|class=skin-invert-image|Widely proposed arrow-pushing mechanism for acid-catalyzed dynamic equilibrium between the α- and β- [[anomer]]s of D-glucopyranose]]
<div class="skin-invert-image">
{{multiple image
| align = right
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| image2 = BETA-D-Glucopyranose V.1.png | width2 = 2608| height2 = 1420
| footer = [[Chair conformation]]s of α- (left) and β- (right) {{small|D}}-glucopyranose
}}</div>
The other open-chain isomer {{small|L}}-glucose similarly gives rise to four distinct cyclic forms of {{small|L}}-glucose, each the mirror image of the corresponding {{small|D}}-glucose.
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===Mutarotation===
▲{{See also|Mutarotation}}
[[File:Mutarotation D-Glucose V.1.png|thumb|upright=2|class=skin-invert-image|Mutarotation: {{sm|d}}-glucose molecules exist as cyclic hemiacetals that are epimeric (= diastereomeric) to each other. The epimeric ratio α:β is 36:64. In the α-D-glucopyranose (left), the blue-labelled hydroxy group is in the axial position at the anomeric centre, whereas in the β-D-glucopyranose (right) the blue-labelled hydroxy group is in equatorial position at the anomeric centre.]]
Mutarotation consists of a temporary reversal of the ring-forming reaction, resulting in the open-chain form, followed by a reforming of the ring. The ring closure step may use a different {{chem2|\sOH}} group than the one recreated by the opening step (thus switching between pyranose and furanose forms), or the new hemiacetal group created on C-1 may have the same or opposite handedness as the original one (thus switching between the α and β forms). Thus, though the open-chain form is barely detectable in solution, it is an essential component of the equilibrium.
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Whether in water or the solid form, {{sm|d}}-(+)-glucose is [[Dextrorotation and levorotation|dextrorotatory]], meaning it will rotate the direction of [[polarized light]] clockwise as seen looking toward the light source. The effect is due to the [[chirality]] of the molecules, and indeed the mirror-image isomer, {{sm|l}}-(−)-glucose, is [[Dextrorotation and levorotation|levorotatory]] (rotates polarized light counterclockwise) by the same amount. The strength of the effect is different for each of the five [[tautomer]]s.
The conversion between the two anomers can be observed in a [[polarimeter]] since pure α-{{sm|d}}-glucose has a specific rotation angle of +112.2° mL/(dm·g), pure β-{{sm|d}}-glucose of +17.5° mL/(dm·g).<ref name=" Hesse">Manfred Hesse, Herbert Meier, Bernd Zeeh, Stefan Bienz, Laurent Bigler, Thomas Fox: ''Spektroskopische Methoden in der organischen Chemie''. 8th revised Edition. Georg Thieme, 2011, {{ISBN|978-3-13-160038-7}}, p. 34 (in German).</ref> When equilibrium has been reached after a certain time due to mutarotation, the angle of rotation is +52.7° mL/(dm·g).<ref name="Hesse" /> By adding acid or base, this transformation is much accelerated. The equilibration takes place via the open-chain aldehyde form.
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In dilute [[sodium hydroxide]] or other dilute bases, the monosaccharides [[mannose]], glucose and [[fructose]] interconvert (via a [[Lobry de Bruyn–Van Ekenstein transformation|Lobry de Bruyn–Alberda–Van Ekenstein transformation]]), so that a balance between these isomers is formed. This reaction proceeds via an [[enediol]]:
[[File:Glucose Fructose Mannose Gleichgewicht.png|frameless|upright=2.0|class=skin-invert-image|Glucose-Fructose-Mannose-isomerisation]]
==Biochemical properties==
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! Metabolism of common [[monosaccharide]]s and some biochemical reactions of glucose
|-
|[[File:Metabolism of common monosaccharides, and related reactions.png|none|1000px|class=skin-invert-image]]
|}
Glucose is the most abundant monosaccharide. Glucose is also the most widely used aldohexose in most living organisms. One possible explanation for this is that glucose has a lower tendency than other aldohexoses to react nonspecifically with the [[amine]] groups of [[protein]]s.<ref name=Higgins>{{cite journal|last1=Bunn|first1=H. F.|last2=Higgins|first2=P. J.|title=Reaction of monosaccharides with proteins: possible evolutionary significance |journal=Science|date=1981|volume=213 |issue=4504|pages=222–24|doi=10.1126/science.12192669|pmid=12192669| bibcode=1981Sci...213..222B}}<!--|access-date=13 May 2015--></ref> This reaction—[[glycation]]—impairs or destroys the function of many proteins,<ref name=Higgins/> e.g. in [[glycated hemoglobin]]. Glucose's low rate of glycation can be attributed to its having a more stable [[#Cyclic forms|cyclic form]] compared to other aldohexoses, which means it spends less time than they do in its reactive [[#Open-chain form|open-chain form]].<ref name=Higgins/> The reason for glucose having the most stable cyclic form of all the aldohexoses is that its [[hydroxy group]]s (with the exception of the hydroxy group on the anomeric carbon of {{sm|d}}-glucose) are in the [[Cyclohexane conformation|equatorial position]]. Presumably, glucose is the most abundant natural monosaccharide because it is less glycated with proteins than other monosaccharides.<ref name=Higgins /><ref name="Stryer 531">Jeremy M. Berg: ''Stryer Biochemie
Glucose is produced by plants through photosynthesis using sunlight,<ref name="photo"/><ref name="Löffler/Petrides 195"/> water and carbon dioxide and can be used by all living organisms as an energy and carbon source. However, most glucose does not occur in its free form, but in the form of its polymers, i.e. lactose, sucrose, starch and others which are energy reserve substances, and cellulose and [[chitin]], which are components of the cell wall in plants or [[fungi]] and [[arthropod]]s, respectively. These polymers, when consumed by animals, fungi and bacteria, are degraded to glucose using enzymes. All animals are also able to produce glucose themselves from certain precursors as the need arises. [[Neuron]]s, cells of the [[renal medulla]] and [[erythrocytes]] depend on glucose for their energy production.<ref name="Löffler/Petrides 195">Peter C. Heinrich: ''Löffler/Petrides Biochemie und Pathobiochemie
Many of the long-term complications of [[diabetes]] (e.g., [[Visual impairment|blindness]], [[kidney failure]], and [[peripheral neuropathy]]) are probably due to the glycation of proteins or [[lipid]]s.<ref>{{citation | title = High Blood Glucose and Diabetes Complications: The buildup of molecules known as AGEs may be the key link | journal = Diabetes Forecast | url = http://forecast.diabetes.org/magazine/features/high-blood-glucose-and-diabetes-complications | year = 2010 | publisher = American Diabetes Association | issn = 0095-8301 | access-date =
===Uptake===
Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins [[T1R2]] and [[T1R3]] makes it possible to identify glucose-containing food sources.<ref name="fca">{{cite web | url=https://foodb.ca/compounds/FDB012530 | title=Showing Compound D-Glucose (FDB012530) - FooDB | access-date=
In order to get into or out of cell membranes of cells and membranes of cell compartments, glucose requires special transport proteins from the [[major facilitator superfamily]]. In the small intestine (more precisely, in the [[jejunum]]),<ref name="Harper 641">Harold A. Harper: ''Medizinische Biochemie
The glucose transporter [[GLUT1]] is produced by most cell types and is of particular importance for nerve cells and pancreatic [[Beta cell|β-cell]]s.<ref name="Löffler/Petrides 199" /> [[GLUT3]] is highly expressed in nerve cells.<ref name="Löffler/Petrides 199" /> Glucose from the bloodstream is taken up by [[GLUT4]] from [[muscle cell]]s (of the [[skeletal muscle]]<ref>{{Cite journal |doi=10.1016/j.cmet.2007.03.006 |pmid=17403369|year=2007|last1=Huang| first1=S.|title=The GLUT4 glucose transporter|journal=Cell Metabolism|volume=5|issue=4|pages=237–52|last2=Czech|first2=M. P.|doi-access=free}}</ref> and [[heart muscle]]) and [[fat cell]]s.<ref>{{Cite book |pmid=25344989|date=2014| last1=Govers|first1=R.|title=Cellular regulation of glucose uptake by glucose transporter GLUT4|series=Advances in Clinical Chemistry|volume=66|pages=173–240|doi=10.1016/B978-0-12-801401-1.00006-2|isbn=978-0-12-801401-1}}</ref> [[GLUT14]] is expressed exclusively in [[testicle]]s.<ref>{{cite journal |last1=Wu |first1=Xiaohua |last2=Freeze |first2=Hudson H. |title=GLUT14, a Duplicon of GLUT3, is Specifically Expressed in Testis as Alternative Splice Forms |journal=Genomics |date=December 2002 |volume=80 |issue=6 |pages=553–7 |doi=10.1006/geno.2002.7010 |pmid=12504846}}</ref> Excess glucose is broken down and converted into fatty acids, which are stored as [[triglyceride]]s. In the [[kidney]]s, glucose in the urine is absorbed via SGLT1 and [[SGLT2]] in the apical cell membranes and transmitted via GLUT2 in the basolateral cell membranes.<ref>{{Cite journal |doi=10.1007/s00125-018-4656-5 |pmid=30132032|pmc=6133168|year=2018|last1=Ghezzi|first1=C.|title=Physiology of renal glucose handling via SGLT1, SGLT2, and GLUT2|journal=Diabetologia|volume=61|issue=10|pages=2087–2097|author2=Loo DDF|last3=Wright|first3=E. M.}}</ref> About 90% of kidney glucose reabsorption is via SGLT2 and about 3% via SGLT1.<ref>{{Cite journal |doi=10.1097/MNH.0000000000000152 |pmc=5364028 |pmid=26125647|year=2015 |last1=Poulsen |first1=S. B. |title=Sodium-glucose cotransport |journal=Current Opinion in Nephrology and Hypertension |volume=24 |issue=5 |pages=463–9 |last2=Fenton |first2=R. A. |last3=Rieg |first3=T. }}</ref>
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===Biosynthesis===
{{main|Gluconeogenesis|Glycogenolysis}}
In plants and some [[prokaryote]]s, glucose is a product of [[photosynthesis]].<ref name="photo">{{Cite web|url=http://www.rsc.org/Education/Teachers/Resources/cfb/Photosynthesis.htm|title=Chemistry for Biologists: Photosynthesis|website=www.rsc.org|access-date=5 February 2018
The metabolic pathway that begins with molecules containing two to four carbon atoms (C) and ends in the glucose molecule containing six carbon atoms is called gluconeogenesis and occurs in all living organisms. The smaller starting materials are the result of other metabolic pathways. Ultimately almost all [[biomolecule]]s come from the assimilation of carbon dioxide in plants and microbes during photosynthesis.<ref name=Voet/>{{rp|359}} The free energy of formation of α-{{sm|d}}-glucose is 917.2 kilojoules per mole.<ref name=Voet/>{{rp|59}} In humans, gluconeogenesis occurs in the liver and kidney,<ref name="Szablewski">Leszek Szablewski: ''Glucose Homeostasis and Insulin Resistance
Glucose also can be found outside of living organisms in the ambient environment. Glucose concentrations in the atmosphere are detected via collection of samples by aircraft and are known to vary from location to location. For example, glucose concentrations in atmospheric air from inland China range from 0.8 to 20.1 pg/L, whereas east coastal China glucose concentrations range from 10.3 to 142 pg/L.<ref>{{
===Glucose degradation===
[[File:Glucose metabolism.svg|thumb|Glucose metabolism and various forms of it in the process.{{pb}}Glucose-containing compounds and [[isomer]]ic forms are digested and taken up by the body in the intestines, including [[starch]], [[glycogen]], [[disaccharide]]s and [[monosaccharide]]s.{{pb}}Glucose is stored in mainly the liver and muscles as glycogen. It is distributed and used in tissues as free glucose.]]▼
{{Main|Glycolysis|Pentose phosphate pathway}}
▲[[File:Glucose metabolism.svg|thumb|Glucose metabolism and various forms of it in the process.{{pb}}Glucose-containing compounds and [[isomer]]ic forms are digested and taken up by the body in the intestines, including [[starch]], [[glycogen]], [[disaccharide]]s and [[monosaccharide]]s.{{pb}}Glucose is stored in mainly the liver and muscles as glycogen. It is distributed and used in tissues as free glucose.]]
In humans, glucose is metabolized by glycolysis<ref>{{Cite journal |doi=10.1042/BSR20160385 |pmc=5293555 |pmid=27707936|year=2016 |last1=Adeva-Andany |first1=M. M. |title=Liver glucose metabolism in humans |journal=Bioscience Reports |volume=36 |issue=6 |pages=e00416 |last2=Pérez-Felpete |first2=N. |last3=Fernández-Fernández |first3=C. |last4=Donapetry-García |first4=C. |last5=Pazos-García |first5=C. }}</ref> and the pentose phosphate pathway.<ref name="Horton">H. Robert Horton, Laurence A. Moran, K. Gray Scrimgeour, Marc D. Perry, J. David Rawn: ''Biochemie''. Pearson Studium; 4. aktualisierte Auflage 2008; {{ISBN|978-3-8273-7312-0}}; p. 490–496. (German)</ref> Glycolysis is used by all living organisms,<ref name="Garrett"/>{{rp|551}}<ref name="Hall">Brian K. Hall: ''Strickberger's Evolution.'' Jones & Bartlett Publishers, 2013, {{ISBN|978-1-449-61484-3}}, p. 164.</ref> with small variations, and all organisms generate energy from the breakdown of monosaccharides.<ref name="Hall" /> In the further course of the metabolism, it can be completely degraded via [[oxidative decarboxylation]], the [[citric acid cycle]] (synonym ''Krebs cycle'') and the [[respiratory chain]] to water and carbon dioxide. If there is not enough oxygen available for this, the glucose degradation in animals occurs anaerobic to lactate via lactic acid fermentation and releases much less energy. Muscular lactate enters the liver through the bloodstream in mammals, where gluconeogenesis occurs ([[Cori cycle]]). With a high supply of glucose, the metabolite [[acetyl-CoA]] from the Krebs cycle can also be used for [[fatty acid synthesis]].<ref>{{Cite journal |doi=10.1007/s00125-016-3940-5|pmid=27048250|year=2016|last1=Jones|first1=J. G.|title=Hepatic glucose and lipid metabolism|journal=Diabetologia|volume=59|issue=6|pages=1098–103|doi-access=free}}</ref> Glucose is also used to replenish the body's glycogen stores, which are mainly found in liver and skeletal muscle. These processes are [[Hormone|hormonally]] regulated.▼
▲In humans, glucose is metabolized by glycolysis<ref>{{Cite journal |doi=10.1042/BSR20160385 |pmc=5293555 |pmid=27707936|year=2016 |last1=Adeva-Andany |first1=M. M. |title=Liver glucose metabolism in humans |journal=Bioscience Reports |volume=36 |issue=6 |pages=e00416 |last2=Pérez-Felpete |first2=N. |last3=Fernández-Fernández |first3=C. |last4=Donapetry-García |first4=C. |last5=Pazos-García |first5=C. }}</ref> and the pentose phosphate pathway.<ref name="Horton">H. Robert Horton, Laurence A. Moran, K. Gray Scrimgeour, Marc D. Perry, J. David Rawn: ''Biochemie'' {{In lang|de}}. Pearson Studium; 4. aktualisierte Auflage 2008; {{ISBN|978-3-8273-7312-0}};
In other living organisms, other forms of fermentation can occur. The bacterium ''[[Escherichia coli]]'' can grow on nutrient media containing glucose as the sole carbon source.<ref name=Voet/>{{rp|59}} In some bacteria and, in modified form, also in archaea, glucose is degraded via the [[Entner-Doudoroff pathway]].<ref>{{cite journal | last1 = Entner | first1 = N. | last2 = Doudoroff | first2 = M. | year = 1952 | title = Glucose and gluconic acid oxidation of Pseudomonas saccharophila | journal = [[J Biol Chem]] | volume = 196 | issue = 2| pages = 853–862 | doi = 10.1016/S0021-9258(19)52415-2 | pmid = 12981024 | doi-access = free }}</ref> With Glucose, a mechanism for [[gene regulation]] was discovered in ''E. coli'', the [[catabolite repression]] (formerly known as ''glucose effect'').<ref name="PMID29330542">
Use of glucose as an energy source in cells is by either aerobic respiration, anaerobic respiration, or fermentation.<ref name="sil"/> The first step of glycolysis is the [[phosphorylation]] of glucose by a [[hexokinase]] to form [[glucose 6-phosphate]]. The main reason for the immediate phosphorylation of glucose is to prevent its diffusion out of the cell as the charged [[phosphate]] group prevents glucose 6-phosphate from easily crossing the [[cell membrane]].<ref name="sil">{{cite journal|last1=Bonadonna|first1=Riccardo C|last2=Bonora|first2=Enzo|last3=Del Prato|first3=Stefano|last4=Saccomani|first4=Maria|last5=Cobelli|first5=Claudio|last6=Natali|first6=Andrea|last7=Frascerra|first7=Silvia|last8=Pecori|first8=Neda|last9=Ferrannini|first9=Eleuterio|last10=Bier|first10=Dennis|last11=DeFronzo|first11=Ralph A|last12=Gulli|first12=Giovanni|title=Roles of glucose transport and glucose phosphorylation in muscle insulin resistance of NIDDM|journal=Diabetes|date=July 1996|volume=45|issue=7|pages=915–25|doi=10.2337/diab.45.7.915|pmid=8666143|s2cid=219249555|url=http://diabetes.diabetesjournals.org/content/45/7/915.full-text.pdf |archive-url=https://web.archive.org/web/20170306131309/http://diabetes.diabetesjournals.org/content/45/7/915.full-text.pdf |archive-date=6 March 2017
In anaerobic respiration, one glucose molecule produces a net gain of two ATP molecules (four ATP molecules are produced during glycolysis through substrate-level phosphorylation, but two are required by enzymes used during the process).<ref>{{citation | title = Medical Biochemistry at a Glance @Google books | url = https://books.google.com/books?id=9BtxCWxrWRoC&pg=PA52 | year = 2006 | page = 52 | publisher = Blackwell Publishing | isbn = 978-1-4051-1322-9 | url-status = live | archive-url = https://web.archive.org/web/20180223145046/https://books.google.com/books?id=9BtxCWxrWRoC&pg=PA52 | archive-date =
{{GlycolysisGluconeogenesis_WP534|highlight=Glucose}}
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In [[yeast]], ethanol is fermented at high glucose concentrations, even in the presence of oxygen (which normally leads to respiration rather than fermentation). This is called the [[Crabtree effect]].
Glucose can also degrade to form carbon dioxide through abiotic means. This has been demonstrated to occur experimentally via oxidation and hydrolysis at 22 °C and a pH of 2.5.<ref>{{
===Energy source===
[[File:Glucose catabolism intermediates de.png|thumb|upright=1.2|class=skin-invert-image|Diagram showing the possible intermediates in glucose degradation; Metabolic pathways orange: glycolysis, green: Entner-Doudoroff pathway, phosphorylating, yellow: Entner-Doudoroff pathway, non-phosphorylating]]
Glucose is a ubiquitous fuel in [[biology]]. It is used as an energy source in organisms, from bacteria to humans, through either [[aerobic respiration]], [[anaerobic respiration]] (in bacteria), or [[Fermentation (biochemistry)|fermentation]]. Glucose is the human body's key source of energy, through aerobic respiration, providing about 3.75 [[kilocalorie]]s (16 [[kilojoule]]s) of [[food energy]] per gram.<ref>{{citation | title = Food energy – methods of analysis and conversion factors | chapter-url = http://www.fao.org/docrep/006/Y5022E/y5022e04.htm | chapter = Chapter 3: Calculation of the Energy Content of Foods – Energy Conversion Factors | series = FAO Food and Nutrition Paper 77 | publisher = Food and Agriculture Organization | location = Rome | year = 2003 | isbn = 978-92-5-105014-9 | url-status = live | archive-url = https://web.archive.org/web/20100524003622/http://www.fao.org/DOCREP/006/Y5022E/y5022e04.htm | archive-date =
Glucose and oxygen supply almost all the energy for the [[brain]],<ref>{{cite web |first = Pramod|last = Dash |url =http://neuroscience.uth.tmc.edu/s4/chapter11.html |title=Blood Brain Barrier and Cerebral Metabolism (Section 4, Chapter 11) |work =Neuroscience Online: An Electronic Textbook for the Neurosciences |publisher =Department of Neurobiology and Anatomy – The University of Texas Medical School at Houston |url-status=dead |archive-url=https://web.archive.org/web/20161117104126/http://neuroscience.uth.tmc.edu/s4/chapter11.html |archive-date=
The glucose in the blood is called [[blood sugar]].
The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100 mg/dL of blood (4 to 5.5 mM). In [[blood plasma]], the measured values are about 10–15% higher. In addition, the values in the [[artery|arterial]] blood are higher than the concentrations in the [[vein|venous]] blood since glucose is absorbed into the tissue during the passage of the [[capillary bed]]. Also in the capillary blood, which is often used for blood sugar determination, the values are sometimes higher than in the venous blood. The glucose content of the blood is regulated by the hormones [[insulin]], [[incretin]] and [[glucagon]].<ref name="Koekkoek" /><ref>{{Cite book |doi=10.1016/B978-0-444-53480-4.00026-6 |pmid=25410233 |year=2014 |last1=La Fleur |first1=S. E. |series=Handbook of Clinical Neurology |volume=126 |pages=341–351 |last2=Fliers |first2=E. |last3=Kalsbeek |first3=A. |title=Diabetes and the Nervous System |chapter=Neuroscience of glucose homeostasis |isbn=978-0-444-53480-4}}.</ref> Insulin lowers the glucose level, glucagon increases it.<ref name="Satyanarayana" /> Furthermore, the hormones [[adrenaline]], [[thyroxine]], [[glucocorticoid]]s, [[somatotropin]] and [[adrenocorticotropin]] lead to an increase in the glucose level.<ref name="Satyanarayana" /> There is also a hormone-independent regulation, which is referred to as [[glucose autoregulation]].<ref>{{Cite journal |doi=10.1002/cphy.c140009 |pmid=25589267 |year=2015 |last1=Bisschop |first1=P. H. |title=Autonomic regulation of hepatic glucose production |journal=Comprehensive Physiology |volume=5 |issue=1 |pages=147–165 |last2=Fliers |first2=E. |last3=Kalsbeek |first3=A.}}</ref> After food intake the blood sugar concentration increases. Values over 180 mg/dL in venous whole blood are pathological and are termed [[hyperglycemia]], values below 40 mg/dL are termed [[hypoglycaemia]].<ref>W. A. Scherbaum, B. M. Lobnig<!--: ''Abschnittstitel
Some glucose is converted to [[lactic acid]] by [[astrocyte]]s, which is then utilized as an energy source by [[brain cells]]; some glucose is used by intestinal cells and [[red blood cell]]s, while the rest reaches the [[liver]], [[adipose tissue]] and [[muscle]] cells, where it is absorbed and stored as glycogen (under the influence of [[insulin]]). Liver cell glycogen can be converted to glucose and returned to the blood when insulin is low or absent; muscle cell glycogen is not returned to the blood because of a lack of enzymes. In [[Adipocyte|fat cells]], glucose is used to power reactions that synthesize some [[fat]] types and have other purposes. Glycogen is the body's "glucose energy storage" mechanism, because it is much more "space efficient" and less reactive than glucose itself.
As a result of its importance in human health, glucose is an analyte in [[glucose test]]s that are common medical [[blood test]]s.<ref>{{Cite journal |pmid=22872934 |year=2012 |last1=Clarke |first1=S. F. |title=A history of blood glucose meters and their role in self-monitoring of diabetes mellitus |journal=British Journal of Biomedical Science |volume=69 |issue=2 |pages=83–93 |last2=Foster |first2=J. R. |citeseerx=10.1.1.468.2196 |doi=10.1080/09674845.2012.12002443|s2cid=34263228 }}</ref> Eating or fasting prior to taking a blood sample has an effect on analyses for glucose in the blood; a high fasting glucose
The [[glycemic index]] is an indicator of the speed of resorption and conversion to blood glucose levels from ingested carbohydrates, measured as the [[area under a curve|area under the curve]] of blood glucose levels after consumption in comparison to glucose (glucose is defined as 100).<ref name="Harvey 366">Richard A. Harvey, Denise R. Ferrier: ''Biochemistry''. 5th Edition, Lippincott Williams & Wilkins, 2011, {{ISBN|978-1-608-31412-6}}, p. 366.</ref> The clinical importance of the glycemic index is controversial,<ref name="Harvey 366" /><ref name="Satyarayana 508">U Satyanarayana: ''Biochemistry''. Elsevier Health Sciences, 2014, {{ISBN|978-8-131-23713-7}}, p. 508.</ref> as foods with high fat contents slow the resorption of carbohydrates and lower the glycemic index, e.g. ice cream.<ref name="Satyarayana 508" /> An alternative indicator is the [[insulin index]],<ref>{{Cite journal |doi=10.1093/ajcn/66.5.1264 |pmid=9356547 |year=1997 |last1=Holt |first1=S. H. |title=An insulin index of foods: The insulin demand generated by 1000-kJ portions of common foods |journal=The American Journal of Clinical Nutrition |volume=66 |issue=5 |pages=1264–1276 |last2=Miller |first2=J. C. |last3=Petocz |first3=P. |doi-access=free}}</ref> measured as the impact of carbohydrate consumption on the blood insulin levels. The [[glycemic load]] is an indicator for the amount of glucose added to blood glucose levels after consumption, based on the glycemic index and the amount of consumed food.
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Organisms use glucose as a precursor for the synthesis of several important substances. Starch, [[cellulose]], and glycogen ("animal starch") are common glucose [[polymer]]s (polysaccharides). Some of these polymers (starch or glycogen) serve as energy stores, while others (cellulose and [[chitin]], which is made from a derivative of glucose) have structural roles. Oligosaccharides of glucose combined with other sugars serve as important energy stores. These include lactose, the predominant sugar in milk, which is a glucose-galactose disaccharide, and sucrose, another disaccharide which is composed of glucose and fructose. Glucose is also added onto certain proteins and [[lipid]]s in a process called [[glycosylation]]. This is often critical for their functioning. The enzymes that join glucose to other molecules usually use [[phosphorylation|phosphorylated]] glucose to power the formation of the new bond by coupling it with the breaking of the glucose-phosphate bond.
Other than its direct use as a monomer, glucose can be broken down to synthesize a wide variety of other biomolecules. This is important, as glucose serves both as a primary store of energy and as a source of organic carbon. Glucose can be broken down and converted into
==Pathology==
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===Hypoglycemia management===
[[File:Soluţie glucoză 5%.jpg|thumb|right|220px|Glucose, 5% solution for [[Infusion therapy|infusion]]s]]
Individuals with diabetes or other conditions that result in [[hypoglycemia|low blood sugar]] often carry small amounts of sugar in various forms. One sugar commonly used is glucose, often in the form of glucose tablets (glucose pressed into a tablet shape sometimes with one or more other ingredients as a binder), [[hard candy]], or [[sugar packet]].
==Sources==
[[File:Glucose 2.jpg|thumb|
Most dietary carbohydrates contain glucose, either as their only building block (as in the polysaccharides starch and glycogen), or together with another monosaccharide (as in the hetero-polysaccharides sucrose and lactose).<ref>{{Cite news|url=https://www.hsph.harvard.edu/nutritionsource/carbohydrates/carbohydrates-and-blood-sugar/|title=Carbohydrates and Blood Sugar|date=5 August 2013
{|class="wikitable sortable" style="text-align:center; margin:auto"
|+ Sugar content of selected common plant foods (in grams per 100 g)<ref name="www.nal.usda.gov">{{Cite web|url=https://fdc.nal.usda.gov/index.html|title=FoodData Central|website=fdc.nal.usda.gov|access-date=18 March 2024
|-
! Food <br />item
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==Commercial production==
Glucose is produced industrially from starch by [[enzyme|enzymatic]] [[hydrolysis]] using [[glucose amylase]] or by the use of [[acids]]. Enzymatic hydrolysis has largely displaced acid-catalyzed hydrolysis reactions.<ref name="Fellows">P. J. Fellows: ''Food Processing Technology. Woodhead Publishing'', 2016, {{ISBN|978-0-081-00523-1}}, p. 197.</ref> The result is glucose syrup (enzymatically with more than 90% glucose in the dry matter)<ref name="Fellows" /> with an annual worldwide production volume of 20 million tonnes (as of 2011).<ref name="Ullmann 48">Thomas Becker, Dietmar Breithaupt, Horst Werner Doelle, Armin Fiechter, Günther Schlegel, Sakayu Shimizu, Hideaki Yamada: ''Biotechnology'', in: ''Ullmann's Encyclopedia of Industrial Chemistry'', 7th Edition, Wiley-VCH, 2011. {{ISBN|978-3-527-32943-4}}. Volume 6, p. 48.</ref> This is the reason for the former common name "starch sugar". The amylases most often come from ''[[Bacillus licheniformis]]''<ref name="ResSoc">The Amylase Research Society of Japan: ''Handbook of Amylases and Related Enzymes
Many crops can be used as the source of starch. [[Maize]],<ref name="Fellows" /> rice,<ref name="Fellows" /> [[wheat]],<ref name="Fellows" /> [[cassava]],<ref name="Fellows" /> [[potato]],<ref name="Fellows" /> [[barley]],<ref name="Fellows" /> sweet potato,<ref name="Davidson">Alan Davidson: ''The Oxford Companion to Food''. OUP Oxford, 2014, {{ISBN|978-0-191-04072-6}}, p. 527.</ref> [[corn husk]] and [[sago]] are all used in various parts of the world. In the [[United States]], [[corn starch]] (from maize) is used almost exclusively. Some commercial glucose occurs as a component of [[invert sugar]], a roughly 1:1 mixture of glucose and fructose that is produced from sucrose. In principle, cellulose could be hydrolyzed to glucose, but this process is not yet commercially practical.<ref name="Ullmann" />
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==Commercial usage==
[[File:Relativesweetness.svg|thumb|class=skin-invert-image|Relative sweetness of various sugars in comparison with sucrose<ref>{{cite web
| url = http://food.oregonstate.edu/learn/sugar.html
| url-status = dead
| access-date =
| archive-date =
| archive-url = https://web.archive.org/web/20110718233541/http://food.oregonstate.edu/learn/sugar.html
| website = food.oregonstate.edu
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| department = Learning, Food Resources
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}}</ref>]]
Glucose is mainly used for the production of fructose and of glucose-containing foods. In foods, it is used as a sweetener, [[humectant]], to increase the [[volume]] and to create a softer [[mouthfeel]].<ref name="Fellows" /> Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of [[alcoholic beverage]]s. Most soft drinks in the US use HFCS-55 (with a fructose content of 55% in the dry mass), while most other HFCS-sweetened foods in the US use HFCS-42 (with a fructose content of 42% in the dry mass).<ref name="fda2014">{{cite web |url=https://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm324856.htm |title=High Fructose Corn Syrup: Questions and Answers |publisher=US Food and Drug Administration |date=5 November 2014
▲Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of [[alcoholic beverage]]s. Most soft drinks in the US use HFCS-55 (with a fructose content of 55% in the dry mass), while most other HFCS-sweetened foods in the US use HFCS-42 (with a fructose content of 42% in the dry mass).<ref name="fda2014">{{cite web |url=https://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm324856.htm |title=High Fructose Corn Syrup: Questions and Answers |publisher=US Food and Drug Administration |date=2014-11-05 |access-date=2017-12-18 |url-status=live |archive-url=https://web.archive.org/web/20180125013538/https://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm324856.htm |archive-date=2018-01-25}}</ref> In Mexico, on the other hand, soft drinks are sweetened by cane sugar, which has a higher sweetening power.<ref>Kevin Pang: [https://web.archive.org/web/20110629002034/http://seattletimes.nwsource.com/html/nationworld/2002076071_coke29.html ''Mexican Coke a hit in U.S.''] In: ''[[Seattle Times]]'', October 29, 2004.</ref> In addition, glucose syrup is used, inter alia, in the production of [[confectionery]] such as [[candy|candies]], [[toffee]] and [[fondant icing|fondant]].<ref name="Beckett">Steve T. Beckett: ''Beckett's Industrial Chocolate Manufacture and Use''. John Wiley & Sons, 2017, {{ISBN|978-1-118-78014-5}}, p. 82.</ref> Typical chemical reactions of glucose when heated under water-free conditions are [[caramelization]] and, in presence of amino acids, the [[Maillard reaction]].
In addition, various organic acids can be biotechnologically produced from glucose, for example by fermentation with ''[[Clostridium thermoaceticum]]'' to produce [[acetic acid]], with ''[[Penicillium notatum]]'' for the production of [[araboascorbic acid]], with ''[[Rhizopus delemar]]'' for the production of [[fumaric acid]], with ''[[Aspergillus niger]]'' for the production of [[gluconic acid]], with ''[[Candida brumptii]]'' to produce [[isocitric acid]], with ''[[Aspergillus terreus]]'' for the production of [[itaconic acid]], with ''[[Pseudomonas fluorescens]]'' for the production of [[2-ketogluconic acid]], with ''[[Gluconobacter suboxydans]]'' for the production of [[5-ketogluconic acid]], with ''[[Aspergillus oryzae]]'' for the production of [[kojic acid]], with ''[[Lactobacillus delbrueckii]]'' for the production of [[lactic acid]], with ''[[Lactobacillus brevis]]'' for the production of [[malic acid]], with ''[[Propionibacter shermanii]]'' for the production of [[propionic acid]], with ''[[Pseudomonas aeruginosa]]'' for the production of [[pyruvic acid]] and with ''[[Gluconobacter suboxydans]]'' for the production of [[tartaric acid]].<ref name="Kent">James A. Kent: ''Riegel's Handbook of Industrial Chemistry''. Springer Science & Business Media, 2013, {{ISBN|978-1-475-76431-4}}, p. 938.</ref>{{additional citation needed|date=April 2022}} Potent, bioactive natural products like triptolide that inhibit mammalian transcription via inhibition of the XPB subunit of the general transcription factor TFIIH has been recently reported as a glucose conjugate for targeting hypoxic cancer cells with increased glucose transporter expression.<ref>{{cite journal | journal = iScience | title = A Glucose-Triptolide Conjugate Selectively Targets Cancer Cells under Hypoxia | volume = 23 | issue = 9 | year = 2020 |vauthors=Datan E, Minn I, Peng X, He QL, Ahn H, Yu B, Pomper MG, Liu JO | page = 101536 | pmid = 33083765 | doi=10.1016/j.isci.2020.101536| pmc = 7509213 | bibcode = 2020iSci...23j1536D }}</ref> Recently, glucose has been gaining commercial use as a key component of "kits" containing lactic acid and insulin intended to induce hypoglycemia and hyperlactatemia to combat different cancers and infections.<ref>{{Cite journal|last1=Goodwin|first1=Matthew L.|last2=Gladden|first2=L. Bruce|last3=Nijsten|first3=Maarten W. N.|date=3 September 2020
==Analysis==
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====Tollens test====
In the [[Tollens test]], after addition of ammoniacal [[Silver nitrate|AgNO<sub>3</sub>]] to the sample solution, glucose reduces Ag<sup>+</sup> to elemental [[silver]].<ref>B. Tollens: [https://babel.hathitrust.org/cgi/pt?id=uiug.30112025692838;view=1up;seq=535 ''Über ammon-alkalische Silberlösung als Reagens auf Aldehyd''] {{Webarchive|url=https://web.archive.org/web/20220219063751/https://babel.hathitrust.org/cgi/pt?id=uiug.30112025692838;view=1up;seq=535 |date=
====Barfoed test====
In [[Barfoed's test]],<ref name="barfoed">{{Cite journal |doi=10.1007/BF01462957 |title=Ueber die Nachweisung des Traubenzuckers neben Dextrin und verwandten Körpern |language=de |journal=Zeitschrift für Analytische Chemie |volume=12 |pages=27–32 |year=1873 |last1=Barfoed |first1=C. |s2cid=95749674 |url=https://zenodo.org/record/1594255 |access-date=1 July 2019
====Nylander's test====
As a reducing sugar, glucose reacts in the [[Nylander's test]].<ref>Emil Nylander: ''Über alkalische Wismuthlösung als Reagens auf Traubenzucker im Harne'', [[Zeitschrift für physiologische Chemie]]. Volume 8, Issue 3, 1884, p. 175–185 [http://www.degruyter.com/dg/viewarticle/j$002fbchm1.1884.8.issue-3$002fbchm1.1884.8.3.175$002fbchm1.1884.8.3.175.xml Abstract]. {{Webarchive|url=https://web.archive.org/web/20150923213720/http://www.degruyter.com/dg/viewarticle/j$002fbchm1.1884.8.issue-3$002fbchm1.1884.8.3.175$002fbchm1.1884.8.3.175.xml |date=
====Other tests====
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====Photometric enzymatic methods in solution====
{{main|Glucose oxidation reaction}}
The enzyme glucose oxidase (GOx) converts glucose into gluconic acid and hydrogen peroxide while consuming oxygen. Another enzyme, peroxidase, catalyzes a chromogenic reaction (Trinder reaction)<ref>{{Cite journal |doi=10.1177/000456326900600108 |title=Determination of Glucose in Blood Using Glucose Oxidase with an Alternative Oxygen Acceptor |journal=Annals of Clinical Biochemistry |volume=6 |pages=24–27 |year=1969 |last1=Trinder |first1=P. |s2cid=58131350 |doi-access=free }}</ref> of [[phenol]] with [[4-Aminoantipyrine|4-aminoantipyrine]] to a purple dye.<ref name="purpuled">{{cite book |
====Photometric test-strip method====
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===Chromatographic methods===
In particular, for the analysis of complex mixtures containing glucose, e.g. in honey, chromatographic methods such as [[high performance liquid chromatography]] and [[gas chromatography]]<ref name="Galant" /> are often used in combination with [[mass spectrometry]].<ref>{{cite journal | last1 = Sanz | first1 = M. L. | last2 = Sanz | first2 = J. | last3 = Martínez-Castro | first3 = I. | year = 2004| title = Gas chromatographic-mass spectrometric method for the qualitative and quantitative determination of disaccharides and trisaccharides in honey. | journal = [[Journal of Chromatography A]] | volume = 1059 | issue = 1–2| pages = 143–148 | pmid = 15628134 | doi = 10.1016/j.chroma.2004.09.095 }}</ref><ref name="mpg-210190">{{cite web|title=Glucose mass spectrum|periodical=Golm Metabolome Database|url=http://gmd.mpimp-golm.mpg.de/Spectrums/8dee81a1-8d98-4a73-b55d-9de42f10e190.aspx|access-date=4 June 2018
====In vivo analysis====
Glucose uptake in cells of organisms is measured with [[2-deoxy-D-glucose]] or [[fluorodeoxyglucose]].<ref name="Dwyer">Donard Dwyer: ''Glucose Metabolism in the Brain
==References==
{{Reflist}}
== External links ==
* {{
{{Diagnostic agents}}
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{{Carbohydrates}}
{{Sugar}}
{{Authority control}}
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[[Category:Glucose| ]]
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[[Category:Nutrition]]
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[[Category:World Health Organization essential medicines]]
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