= ‘a
Poy rmesose
Ft
pas the molecular formula CylH,.05. On
a tte ‘pemical propertics it was found :
q Pentain aketonic functional group CH2OH
fe
: : <0
1 yeastraight chain of six carbon Holy
Hon
pe ne case of glucose.
i .
jbl Song to D-series and a y_4_
{1 compound: Therefore, it is L =
sity written as D-(-)-fructose. ts ppt,
(tt soture is shown on R. H. S,
port structure for Fructose. Like gl
ne struc slucose,
forms internal ketal by the intramolecular
2 stketo group and ~ OH group of Gg atom, As
ey exomes chiral. Thus, fructose has two possible
D- (-) fructose and f-D--) fructose which
gs a
4 i arrangement of ~ CH,OH and -OH groups
fies.
‘These two isomers are shown in Fig. 17.3.
B-D-Fructose
4 4
a 6
4 4 e
G _ a
oO 1 CHZOH
rz Gy ie
on OHH
a-D-Fructose fee neep
Fig. 17.3 Structure of « and B-D(-) fructose.
Inthe free state, D-fructose exists as a six membered
Zot as pyranose ring as shown in Fig.17.3. However, in
‘onbined state as a constituent of disaccharides, it exists
befuranose form (5-membered hemiketal) as shown in
-N14 and 17.5, Tt ean be obtained by internal ketal
re by combining keto group (of C-2) and-OH group
s|
6|
HOH ‘CH2OH
sg. iotranose [casera
24Fschor projection formulae of a andP-fructoturanose:
-0-Fructose
Fig.17.5 Howarth projection. formutae deka ats
‘end tructoturanose
‘These cyclic structures ean also be
writ
tae written in the same
Uses of (-) Fructose. Fructose is used
(i) as a substitute for cane sugar by diabetic patients,
(ii) as a sweetening agent in confectionary.
DISACCHARIDES
ey Disaccharides are the compounds which on hydrolysis,
with dilute acids or enzymes yield two molecules of either
same or different monosaccharides, e.g.,
CigH20}1 + HO Coty + CoH 20
Matos Glucose” QLACO DL,
CygH 30), + H90 > CgHy206 + CoH 1206
Suctone Gucwe” Frise
CigHy:041 +20 > Celta + CoH i206
Lactose Giucose” — Galaciose
‘These are formed by the condensation reaction between
two molecules of the same or different monosaccharides
and involve the formation of an acetal from a hemiacetal
and an alcohol with the elimination of the water. In this
reaction, one molecule of the monosaccharide acts as the
hemiacetal while the other acts as the alcohol. The new
linkage formed is called the glycosidic linkage. X/“”
The disaccharides may be reducing or non-reducing depending
upon the position of glucosidic linkage between two
monosaccharide units. Ifthe glycosidic linkage is formed
between the carbonyl functions of both the monosaccharide
units, the resulting disaccharide would be non-reducing, €.8.
sucrose. If one of the carbonyl functions in any one of the
monosaccharide units is free, the resulting disaccharide would
be reducing in nature, e.g., maltose and lactose.
Sucrose (Cane Sugar), CyzH22011
‘Sucrose (ordinary table sugar) is the most common
icaccharide widely distributed in plants. It occurs in sugar
one (16-20%), agar beets (10-15%), pine apples
(10-12%), apricot, banana, mango and honey. It is
tnanufactured from sugar cane (which grows in tropical
Countries like India and Java) or beet root (which grows in
cold climates).
Sucrose is a colourless, odourless, crystalline sweet
substance having mp, 185-186°C. It is soluble in water
but practically insoluble in alcohol and ether.
Inversion of sugar. Sucrose is dextrorotatory with
a specific rotation, [aly = + 66.5°. On hydrolysis in
presence of HCl or enzyme invertase or sucrasem, it givesan equimolar mixture of glucose with a specific rola/i0®
aly = + 52.7 and fructose with a specific rotation, [@'p
= ~ 924°, Since the specific rotation of D(+) glucosé 18
Tess than that of D-C) fructose, the resulting solution afte?
hydrolysis becomes laevorotatory. Since the hydrolysis ©,
suerose to an equimolar mixture of D-(+) glucose ant,
(D)-() fructose is accompanied by the change in sien ©
optical rotation from dextrorotatory to laevorotatoryy
hydrolysis of sucrose is called inversion of sugar an
the equimolar mixture of D-(+) glucose and D-(-) fructose
obtained as a result of hydrolysis is called invert sugar.
CygHax0)) + HO AS CoH 1206 + ColHl126
[al = +665 rye Dyt)-Civeose _ D-CIFroetose
[alp = +527 [aly =-924
Fermentation. Aqueous solution of sucrose on
fermentation with yeast, gives ethyl alcohol and carbon
dioxide. The enzyme invertase (present in yeast) first
converts sucrose into glucose and fructose. Another enzyme
zymase (also present in yeast) then converts glucose and
fructose into ethyl alcohol with the evolution of carbon
dioxide.
CygHa2011 + H20 FP Cott 206 + CoHi206
Bere Ghusoe Fructose
C6Hj20, 2+ 2C) HOH +2C0)
It may also be noted that sucrose does not act as
reducing agent and does not form anycyanohydrin or oxime
Structure. Sucrose on hydrolysis yields a mixture
of equal parts of glucose and fructose. This shows that
sucrose molecule is made by the combination of one glucose
and one fructose molecule with the elimination of a water
molecule as shown in Fig. 17.6. These two monsaccharides
gfe held together by glycosidic linkage between C; of
on
Ghessae
ieee
cHeOH
@-D-Frictotzaroce)
‘a
Hodg b
° Ho
nfo
woe
pow TE
Hcy
i 4
ch
SC CHEMISTRY pp
cy of fefructose. Since, the reduc
cogs nd oe oee are involved in glyeosige =
of gluston, sucrose is a non-reducing SUN ns
(Ornerges of Sucrose. Sucrose is used =
toaa food and as a sweetening agent,
(Ot a preservative for food prods such as Jay,
dips the laboratory preparation of oxalic aig, ™
(Gay for denaturing alcohol and to render pop,
transparent and oil repellant. :
Meats.) Charring test. Take a pinch ofthe organ
compound and add to it 1 mL of cone. HaS0,, Chains
place. Tarvin
takes oD Led acetate test. To mL of aqueous solution of
the compound, add 1 mL of lead acetate solution and exes,
of NH,OH-A white ppt.
in Nickel sulphate test. Boil 0.1 gof the compoung
with canmoniaeal nickel sulphate solution Add di H,so,
Solution - a red colour. "
tiv) Cobalt nitrate test. Warm 1 mL of the aqueous
solution of the compound with 1 mL of NaOH solution and
Solew drops of cobalt nitrate solution -a violet
colouration.
ole ose (Malt Sugar), CyzH22011
Itis obtained by the partial hydrolysis of starch by
diastase, an enzyme present in malt which is obtained from
sprouted barley seeds.
2(CH 90s). + HO PB nC 2H320),
‘stch ; Matoxe
Maltose on hydrolysis yields two molecules of
a-D-(+) glucose. This indicates that maltose (malt sugar)
is formed by the condensation of two molecules ofa-glucose
in which C, of one a-glucose unit is connected to C, of the
other through an a-glycosidic linkage.
RT
Fig. 17.7 Formation and structure of maltose.gouotecuLes
poth glucose units are in pyranose form and maltose
pequeing sugar. The form, ind structure of
is 8 "is shown in Fig, 17.7,
AZ (Milk Sugat), CypH920 sy
actase ovcurs in the milk ofall animals and is also
% gi milk sugar: Cow's milk contains 4 to 6 pereent and
‘an milk contains 5 to 8 percent lactose. Unlike other
wichyadrates, it is not found in plants.
Lactose on hydrolysis with dilute acid or emulsin
enzyme which specifically hydrolyses p-glycosidie
1H ages) produces one molecule of f-D-galactose and one
ule of B-D-glucose. This indicates that lactose is
ined by combining a glucose unit and a galactose unit
ih the elimination of water as shown in Fig. 17.8. The
sniage is between C of galactose and Cy of glucose, Hence,
jose is called a reducing sugar.
ED 800015 wit rtatve swoctnss,
‘Sugar Relative ‘Sugar Relative
‘Sweetness ‘Sweetness
Fructose 173 Galactose 82
Sucrose 100 Maltose 32
Glucose 14 Lactose 16
GA YOLYSACCHARIDES
hy
‘hese compounds give a very lar;
a /e a very large number of
‘monosaccharide molecules on acidie hydrolysis, Cellulose
and starch are two important examples of polysaccharides
heir general formula is (CeHjgO,), where n isan intogey
having very high value
(CoH o0s),, + 0,0 nC gH,.05
Starch or elalove Gucose
Polysaccharides are generally amorphous, tasteless
substances which are insoluble in water. On complete
hydrolysis in presence of acids or enzymes, they change
into monosaccharides.
‘Three important examples of the polysaccharides are:
starch, cellulose and glycogen.
Starch (Amylum), (CgH,g05),. It occurs in plants
inthe form of granules which are found mainly in the seeds,
fruits, tubers and roots of the plants. It is a mixture of two
polysaccharides, i.e, amylose (20%) and amylopectin (80%).
Amylose is water soluble while amylopectin is insoluble.
Both amylose and amylopectin are polymers of glucose.
Amylose is composed of 1003000 D-glucose units linked
together to form unbranched chains. On the other hand,
Fig. 17.8 Formation and structure of -Lactose.
Tsucar AND SWEETNESS
Mono as well as disaccharides are sweet in taste.
“rent sugars have different degree of sweetness. Fructose
the sweetest sugar known (see Table 17.2). Some
fuPounds like saccharine which has different chemical
‘ure from carbohydrates is 500 times sweeter than
wis? and is used as artificial sweetner. Some proteins
Si Peptides are sweeter than sugars. For example,
‘kul protein is 2000 times sweeter than sucrose
‘spartame peptide is 160 times sweeter than sucrose.
amylopectin is a branched chain polysaccharide made up
of 25-30 D glucose units joined by a-glycosidic linkages
H=o: between C-1 of one glucose unit'and C, of the next glucose
se Meeay unit as in amylose. However, thé6 chains are connected to
lee ° each other by 1, 6-linkages.|The structure of amylose and
° Ho-c—H amylopectin are shown in Fig. 17.9 (a) and (6) respectively.
| uA 5 y HA
cH ‘i ti (]
i moQ OH HW HH om
GH0H en Fete SE fae YE
#-D-Glactose -D-Glicose
Amylose is near polymer of a-D-gucose unts
Fig. 17.9(a) Structure of amylose
Amylopeetinis a branched chain polymer
Fig. 17.9(b) Structure of amylopectin
Tt may be noted that no ‘wo sour
starch eder, insoluble
Starch is a white amorphous powder, nso
in cold water. Its solution in water gives a blue CmeNr
with iodine solution. Theblue colour disappearsan Henle
and reappears on cooling, On hydrolysis with dite
or enzyme, starch breaks down to smaller molocr ee
maltose and finally D-glucose. Stareh is @ major food
material and is hydrolysed by enzyme amylose pres
saliva, The end product is glucose.
(CoH 00s) > (Col oOs)at > Cr2H-
rend) :
Starch does not reduce Fehling solution oF Tolan’
reagent and does not form an osazone. This indicates that
all hemiacetal hydroxyl groups of glucose units (C - 1) are
linked with glycosidic linkages.
It is used as food in the form of bread, cakes, rice and
potatoes. It is used in the manufacture of glucose, ethyl
alcohol, dextrins and adhesives. Starch is also used in
coating and sizing paper to improve its writing qualities. It
is also used for stiffening textiles, Starch is used as an
indicator for iodometric titrations. The structure of amylose
and amylopectin are shown in Fig. 17.9(a) and (b) respectively.
Inaddition to starch, many polysaccharides like gum
and peetins are used as food components. Gums are
polysaccharides which are made up of more than one type
of monosaccharides. Gum arabic is available from trees and
shrubs. These cause gelling and are used in food industry
for the purpose of thickening and improvement to texture.
Some gums are used as inert agents (in drug preparation)
to suspend an active drug.
Difference between gums and other polysaccharides
(© Gums are polysaccharides which are made up of
more than one type of monosaccharides whereas othor
Polysaccharides are made up of only one type of mono.
saccharides,
Gums are acidic polysaccharides whereas other
‘Charides are neutral.
vs give identical
33041 > Calli 206
Ee bine
Pol
GEWD vitterence between Monosaccharides,
18C CHEMIsy yy
"
ate nest glucans anit CFE ITO), hy Pony
a ep 00 to 6,000,000 correnpond he
5 of 50,000 (0 6,00
rise units joined Cogetlyer® Wood iin
glucose U
and
cellule:
GHyOH bon
oN % 0
Wy
1
HM
4
on At
Wo F Gn
LG Pi
Hon Mtn
Fig. 17.10 Structure of collulose
Ti malay
N through multiple hydrogen bonds.‘
arith its structure due to which it ean be used tet
1s a cell wall material, ny
Cellulose is a colourless amorphous sol Whi
decomposes on heating, It does not reduce Tollen', reaga
and Fehling’s solution, It does not form osszone nat
fermented by yeast Ttis not hydrolysed so easily aan
However, on heating with dilute sulphuric acid uxge
pressure, it yields D-glucose as the only product
Cellulose is used in the preparation of some imprtay
products :
Us Gun Cotton (explosive).
Bir As cellulose acetate-ysed in plastics, raping
films, nail polish etc.
(iii) As ethyl cellulos¥ tf plastic coats and films,
Gv) As methyl cellulose in fabric sizing, cosmeticsand
pastes,
() Celluloid and rayons.
Peetins. These are found in fruit skins and are
extracted by boiling them in water. Citrus rends contain
50% pectin. Jelly is prepared by dissolving pectin in rut
juice. Here pectin helps jelly to set into a semisolid Pein
finds use in drug preparation as inert agent to suspend an
fe drug.
Glycogen. The polymer consists of hundred to
thousand units of glucose. It is the main form in sich
slucose is stored in the body. Glycogen mainly oocurs in
the oh and liver. It is a short term food reserve in
animals fs structure is similar to that of amylopecti
iffer fen eCcharides, disaccharides and polysacch
differ from each other in many respects. The main points
of differences are given in Table 17.3.
disaccha ;
ee tence Disaccharides es tates
eit general formula is|Thelr ; olysaccharides
CrHa90, where n is be Grnerel formula is| These are eithe 5(C. ), called
are trees ea faa ae C
bon wE8 contain 3 to 7 These si hexosans :
carbon atoms, moneeanstts eentain twolThese contain m, ides linked
iccharide units together by aiecaae monosacchari haa al
et ee c linkage in a long
cture.