Quiz(5%)

1. Define Biochemistry.
2. List the correct molecular hierarchy of cell
3. Mention at least two roles of Biochemistry in
medical and health sciences.
4. Buffer is a solution made of ……….. & ………
5. Write the three buffer systems which are found in
our body.
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CARBOHYDRATEs
By: Amanuel Wotera, 2024
Introduction of carbohydrates
 The term ‘carbohydrate’ was originally expressed as ‘hydrates
of carbon’ or could be represented by the general formula,
Cx(H2O)y or CnH2nOn .
- But some carbohydrates like deoxyribose (C5H10O4) and
rhamnose (C6H12O5) do not have the required ratio of hydrogen to
oxygen.
- In addition, certain carbohydrates are known to possess
nitrogen (e.g., glucosamine, C6H13O5N), phosphorus or sulfur and
obviously do not coincide with the above general formula.

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Intro Cont’d…

- Formaldehyde (CH2O), acetic acid (C2H4O2) and lactic acid

(C3H6O3) which have C, H and O and the ratio of H : O is also the
same as in water, but are not a carbohydrates.
- Hence, the continued usage of the term ‘carbohydrate’ is for
convenience rather than exactness.
 Carbohydrates are also known as saccharides (sakcharon =
sugar or sweetness) since many of those of relatively small
molecular weight have a sweet taste.

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 Intro cont’d…
 Nowadays, the carbohydrates are broadly defined as
polyhydroxy aldehydes or ketones and their derivatives or
substances that yield one of these compounds on hydrolysis.
- Plants are considerably richer in carbohydrates in comparison
to the animals.
- On the basis of mass, carbohydrates are the most abundant
biomolecules on Earth. Each year, photosynthesis converts
more than 100 billion metric tons of CO2 and H2O into cellulose
and other plant products.

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Functions of Carbohydrates
 Major source of energy
 Storage form of energy molecule for animals and plants.
 Glycans (polysaccharides) are component of structure in
- Animal skin, connective tissue, tendons, cartilage and
- Cell walls of bacteria (peptidoglycan) & plants (cellulose)
 Lubricant of skeletal joints
 Involve in cell-cell interaction
 Structural components of nucleic acids (RNA ,DNA & other
nucleotides).
 Metabolic precursors of proteins , nucleotides, coenzymes, fatty
acids.

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Classification of Carbohydrates

Grouped into three types based on number of sugar units joined

through glycosidic bonds
 Monosaccharides (simple sugars): are simplest form of sugars,
which cannot be further hydrolyzed (building units and hydrolytic
end products of the more complex carbohydrates).
- are either aldehydes or ketones with two or more hydroxyl groups.

- Their general formula is Cn(H2O)n or CnH2nOn.

- Many of the carbon atoms to which hydroxyl groups are attached

are chiral centers, which give rise to the many sugar stereoisomers
found in nature.
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Cont’d…
- Monosaccharides are colorless, crystalline solids that are freely
soluble in water but insoluble in nonpolar solvents.
- Most have a sweet taste.

- except fructose, ketoses are not as common as aldoses. The most

abundant monosaccharide in nature is the 6- carbon sugar, D-
glucose.
- The aldopentoses D-ribose and 2-deoxy-D-ribose are components
of nucleotides and nucleic acids.
- Monosaccharides containing 3 to 9 carbon atoms occur in nature.
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 Cont’d…
Oligosaccharides
 These are the conjugates of carbohydrates where 2-10
monosaccharide units are linked to each other.
- These are compound sugars that yield 2 to 10 molecules of the same
or different monosaccharides on hydrolysis.
- Accordingly, an oligosaccharide yielding 2 molecules of
monosaccharide on hydrolysis is a dissaccharide, and the one
yielding 3 molecules of monosaccharide as a trisaccharide and so on.
- The general formula of disaccharides is Cn(H2O)n – 1 and that of
trisaccharides is Cn(H2O)n – 2 and so on.
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Oligosaccharide cont’d…
• A few examples are :
 Disaccharides – sucrose, lactose, maltose, cellobios,
Trehalose, Gentiobiose, melibios
 Trisaccharides – Rhamninose, Gentianose,
Raffinose(=Melitose), Rabinose, Melezitose.
 Tetrasaccharide – Stachyose, Scorodose
 Pentasacharide – Verbascose
 Molecular composition of few oligosaccharides:
- Raffinose –α-Galactose (1–6) α-Glucose (1–2) β-Fructose
- Stachyose – α-Galactose (1–6) α-Galactose (1–6) α-Glucose
(1–2) β-Fructose
- Verbascose – α-Galactose (1–6) α-Galactose (1–6) α-Galactose
(1–6) α-Glucose (1–2) β-Fructose.

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 Polysaccharides or Polysaccharoses (poly = many)
 These are higher polymers of carbohydrates and contain more
than 10 monosaccharide units per molecule.
 These may be further classified depending on whether the
monosaccharide molecules produced as a result of the
hydrolysis of polysaccharides are of the same type
(homopolysaccharides) or of different types
(heteropolysaccharides).
 Their general formula is (C6H10O5)x.

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Naming of monosaccharides
Monosaccharides have common (trivial) names and systematic
names. Systematic name indicates both the number of carbon
atoms present and aldehyde or ketone group.

1. According to the presence of aldehyde or ketone group:

Aldose Vs ketose

2. According to the number of carbon atoms:

Trioses, Tetroses, Pentoses, Hexoses, Heptoses

3. Combination of both aldehyde or ketone groups with the

number of carbon atoms named as:

Aldotrioses
12/14/2024
Vs ketotrioses, aldohexoses Vs ketohexoses etc. 12
Classification of monosaccharides with its corresponding examples

1. Trioses: monosaccharides containing 3 carbons

a) aldotriose: Glyceraldehyde
b) ketotriose: Dihydroxyacetone
2. Tetroses: monosaccharides containing 4 carbons.
a) aldotetrose: Erythrose
b) ketotetrose: Erythulose: the suffix –ulose is for ketone
group
3. Pentoses: monosaccharides containing 5 carbons.
a) aldopentoses: Ribose, arabinose, xylose and lyxose
b) ketopentoses: Ribulose and xylulose
4. Hexoses: monosaccharides containing 6 carbons.
a) aldohexoses: Glucose, mannose and galactose
b) ketohexoses: fructose
5. Heptoses: monosaccharides containing 7 carbons
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a) Ketoheptose: Ex. Sedoheptulose.
Fig. Examples of monosaccharides found in humans, classified
according to the number of carbons they contain

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D-Aldoses

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D-Ketoses

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 PROPERTIES OF MONOSACHARIDES
 Isomerism
 The term isomer (isosG = equal ; merosG = part) was originally
applied by Jönes Jacob Berzelius, in 1827, to different compounds
with the same molecular formula, and the phenomenon was
called isomerism.
 The isomers are of 2 types : structural isomers and stereoisomers.
- Structural isomers have the same molecular formula but possess
different structures. The difference in structure may be
exhibited either in the length of the carbon chain (chain isomers)
or in the position of a substituent group (positional isomers) or
in possessing different functional groups (functional-group
isomers).
- Stereoisomers - have the same molecular formula and the same
structure but differ only in spatial configuration.
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Cont’d…
• Stereoisomers are of 2 types :
- geometrical and
- optical.
• Geometrical or cis-trans (cisL = same side; transL = across)
isomers. Ex:

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 Optical isomerism
• All the monosaccharides except dihydroxyacetone contain at least
one asymmetric(chiral) carbon atom and hence they exhibit
optical isomerism. The two optical isomers of sugars are D- and L.
• D-form - has H atom at penultimate carbon projected to the left
side and OH group to the right whereas L-form has H atom at
penultimate carbon projected to the right side and OH group to
the left.
• Though both forms of sugars are present in nature, D-isomer is
abundant and sugars present in the body are all D-isomers. L-
fructose and L-rhamnose are two L-isomers found in animals and
plants.

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 Optical isomerism cont’d…
• The two D- and L-forms of a compound constitute a pair of
enantiomers (enantiosG = opposite) or
enantiomorphs(enantiomers(mirror images of a given sugar).
• Thus, D-erythrose and L-erythrose are enantiomers; also D-
glucose and L-glucose.
• The enantiomers (also called optical isomers or double image
isomers) are non-superimposable mirror images of each other
but are chemically identical in their reactions. They agree in their
melting points, solubility etc., but differ in their ability to rotate
the plane of polarized light in a polarimeter; a solution of one of
the two enantiomers rotates the plane to the right, and a solution
of the other to the left.

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Fig: Three ways to represent the two enantiomers of glyceraldehyde.21
Cont’d….
• isomers but not mirror images of each other – are called
diastereoisomers i.e., . In fact, diastereoisomers are different
forms of a compound with two asymmetric centres.
• Diastereoisomers - differ from each other in their melting points,
solubilities and the chemical properties, in general.
• In general, a molecule with n chiral centers can have 2n (two the
power of n) stereoisomers.
- Glyceraldehyde has 2 the power of 1 = 2;
- the aldohexoses, with four chiral centers, have 2 the power of 4 =
16.
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  Optical activity
• Monosaccharides except dihydroxy acetone exhibit optical activity
because of the presence of asymmetric carbon atom.
• If a sugar rotates plane polarized light to right then it is called as
dextrorotatory and if a sugar rotates the plane polarized light to
the left then it is called as levorotatory.
• Usually ‘+’ sign or ‘d’ indicates dextrorotation and ‘–’ sign or l
indicates levorotation of a sugar.
• For example, D-glucose which is dextrorotatory is designated as
D(+) glucose and D-fructose, which is levorotatory is designated
as D(–) fructose. The letter ‘D’ does not indicate whether a given
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sugar is dextro or levorotatory.
  Epimerism
 Epimers are carbohydrate isomers that differ in configuration
around only one specific carbon atom.
Example: - glucose and galactose are C-4 epimers
- Glucose and mannose are C-2 epimers.
- Ribulose and xylulose are C-3 epimers
 However, galactose and mannose are NOT epimers—they differ
in the position of –OH groups at two carbons (2 and 4) and are,
therefore, defined only as isomers

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 Cyclization(ring structure)
• In aqueous solution, aldotetroses and all monosaccharides with
five or more carbon atoms in the backbone occur predominantly
as cyclic (ring) structures in which the carbonyl group has formed
a covalent bond with the oxygen of a hydroxyl group along the
chain.
• In solution, the functional aldehyde group of glucose combines with
hydroxyl group of 5th carbon atom. As a result a 6 numbered
heterocyclic pyranose ring structure containing 5 carbons and
one oxygen is formed.
• Similarly, a 5 numbered furanose ring structure is formed from
fructose when keto group combines with hydroxyl group on 5
carbon atom.
• The linkage between aldehyde group and alcohol is called as
‘hemiacetal’ linkage. The linkage between keto and alcohol
group is called ‘hemi ketal’ linkage.
• Both hemiacetal and hemi ketal are internal or intra molecular 26
 Cyclization cont’d…
• The reaction with the first molecule of alcohol creates an additional
chiral center (the carbonyl carbon). Because the alcohol can add in
either of two ways, attacking either the “front” or the “back” of the
carbonyl carbon, the reaction can produce either of two
stereoisomeric configurations, denoted α and β .
• For example, D-glucose exists in solution as an intramolecular
hemiacetal in which the free hydroxyl group at C-5 has reacted
with the aldehydic C-1, rendering the latter carbon asymmetric
and producing two possible stereoisomers, designated α and β.
• Isomeric forms of monosaccharides that differ only in their
configuration about the hemiacetal or hemiketal carbon atom are
called anomers, and the carbonyl carbon atom is called
the anomeric carbon.

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Fig: Anomers of glucose

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 Cyclization cont’d…
• Six-membered ring compounds are called pyranoses because
they resemble the six-membered ring compound pyran. The
systematic names for the two ring forms of D-glucose are
therefore α-D-glucopyranose and β-D-glucopyranose.
• Ketohexoses (such as fructose) also occur as cyclic compounds
with α and β anomeric forms. In these compounds the hydroxyl
group at C-5 (or C-6) reacts with the keto group at C-2, forming a
furanose (or pyranose) ring containing a hemiketal linkage.
• D-Fructose readily forms the furanose ring ; the more common
anomer of this sugar in combined forms or in derivatives is β -D-
fructofuranose. 29
Fig: ring structure formation 30
Fig: Pyranoses and furanoses
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 Mutorotation
• Monosaccharides containing asymmetric carbon atom rotate plane
polarized light. When optical rotation for α-D-glucose is measured
it will be 112° and on standing the rotation decreases slowly and
attains a constant value +52.5°. Likewise when optical rotation for
β-D-glucose is measured the rotation changes from initial +19° to
+52.5°.
• The change in optical rotation when either form of glucose is
allowed to stand in solution is called mutarotation.
• It is due to conversion of cyclic form of glucose to straight chain
form.

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 Disaccharides
 Lactose = galactose + glucose

- Lactose is synthesized in mammary gland and hence it occurs in milk.

 Sucrose = glucose + fructose

- Ripe fruit juices like pineapple, sugar cane, juice and honey are rich
sources for sucrose. It also occurs in juices of sugar beets, carrot roots
and sorghum.
 Maltose = glucose + glucose

 Maltose is present in germinating cereals and in barley. It may also

formed during the hydrolysis of starch.
 The bonds that link sugars are called glycosidic bonds.
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Polysaccharides
 Contain >10 monosaccharide units per molecule.
 Are high molecular weight polymers.
 Major form of carbohydrates occurring in nature.

Classified into two categories according to the types of monomers:

 Homopolysaccharides: that are composed of one type of
monosaccharide. Ex. Starch, cellulose, glycogen, inulin, dextran
and chitin – made of glucose
 Heteropolysaccharides: that are composed of more than one
type of monosaccharides.
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 Hetropolysaccharides
 Are called as mucopolysaccharides and glycosaminoglycans.
 Mucopolysaccharides consist of repeating units of two types
monosaccharides.
 component of connective tissue, extracellular matrix of bone,
cartilage and tendons. Hence, they are often referred as structural
polysaccharides
 Found in mucous secretions
 It also function as lubricants and shock absorbers.
 The complex of mucopolysaccharide and protein is called as
proteoglycan. 35
Few important mucopolysaccharides or glycosaminoglycans

(GAGs) are:

1. Hyaluronic Acid (HA)

2. chondroitin-4-sulfate and chondroitin-6-sulfate

3. Heparin

4. Dermatan Sulfate

5. Keratan sulfates I and II

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GLYCOPROTEINS
 are proteins containing short chains of carbohydrates.
 The carbohydrate chains are usually oligosaccharides
 These oligosaccharide chains are attached to proteins by
O-glycosidic and N-glycosidic bonds
 are found in mucous fluids, tissues, blood and in cell
membrane.

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DIGESTION OF DIETARY CARBOHYDRATE

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 Digestion of dietary carbohydrate
• The principal sites of dietary carbohydrate digestion are the
mouth and intestinal lumen.
• This digestion is rapid and is catalyzed by known
glycosidases enzymes that hydrolyze glycosidic bonds.

• The final products of carbohydrate digestion are the

monosaccharides, glucose, galactose and fructose, which are
absorbed by cells of the small intestine.

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 1. Carbohydrate digestion in the mouth
Saliva contains a salivary -amylase (ptyalin) produced by the salivary
glands.
During mastication, salivary α-amylase acts briefly on dietary starch
and glycogen, hydrolyzing random α(1→4) bonds and produce
maltose and dextrins.
2. Carbohydrate digestion in the stomach

Salivary -amylase continues to act on starch, glycogen or dextrins for

only 2 - 3 minutes and becomes ineffective because of the extreme
acidic pH

There is no carbohydrate-splitting enzyme in the stomach; however, HCl

hydrolyzes polysaccharides and disaccharides, particularly, sucrose into
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glucose and fructose.
 3.Carbohydrate digestion in the small Intestine
 In the small intestine, there are two things that digest
carbohydrates:
A. The pancreatic juice:
- Neutralize the acidic stomach contents that reach the small
intestine, by bicarbonate secreted by the pancreas, and pancreatic
α-amylase continues the process of starch digestion.
B. Intestinal mucosal brush border enzymes
- The final digestive processes occur primarily at the mucosal lining
of the upper jejunum, and include the action of several
disaccharidases. 41
 Disaccharidases in small intestine include:

• Isomaltase cleaves the α(1→6) bond in isomaltose

• Maltase cleaves maltose and produce glucose
• Sucrase cleaves sucrose producing glucose and fructose
• Lactase (β-galactosidase) cleaves lactose producing galactose and
glucose.
• Trehalase cleave - Trehalose, an α(1→1) disaccharide of glucose
found in mushrooms and other fungi.

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 4. Absorption of monosaccharides by intestinal
mucosal cells
 The duodenum and upper jejunum absorb the bulk of the
dietary sugars.
 However, different sugars have different mechanisms of
absorption.
- For example, galactose and glucose are transported into the
mucosal cells by an active, energy-requiring process that
requires a concurrent uptake of sodium ions; the transport
protein is the sodium-dependent glucose cotransporter 1 (SGLT-
1).
 Fructose uptake requires a sodium-independent
monosaccharide transporter (GLUT-5) for its absorption.
 All three monosaccharides(Glucose, galactose and fructose) are
transported from the intestinal mucosal cell into the portal
circulation by yet another transporter, GLUT-2 43
Fig. Digestion of
carbohydrates
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