TETRAS Educare Study Notes Vol 28 Carbohydrates

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Educare Educare Educare Educare

Compiled By:
Shanmugam V. M.
Faculty, Dept. of Biotech.,
Jyoti Nivas College
Hosur Road,
Bangalore 5! !"5.
proheli#.s$s%g$ail.co$

BIOMOLECULES BIOMOLECULES BIOMOLECULES BIOMOLECULES
PART PART PART PART 1 11 1
CARBOHYDRATES CARBOHYDRATES CARBOHYDRATES CARBOHYDRATES

Not for private circulation, only for JNC students, Not for private circulation, only for JNC students, Not for private circulation, only for JNC students, Not for private circulation, only for JNC students,
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2
Study handout for life science aspirants

CARBOHYDRATES (also known as Saccharides)
Introduction
Carbohydrates are one of important Biomolecules widely distributed in all living
organism and it perform various cellular functions. More than half of the biomass is made
up of carbohydrates. These are synthesized mainly by photosynthetic activity of
photosynthetic organism and plants.
The carbohydrates are compounds containing the carbon, hydrogen and oxygen.
Apart from these some carbohydrates even have itrogen and !ulphate also. These are
commonly called as hydrates of carbon or saccharides "saccharum # sugar$. The chemical
composition of carbohydrates is made of C% &% ' in the ratio of (% )%( hence the general*
empirical formula for carbohydrates is C
n
"&
)
'$
n
.
Definition:
Carbohydrates are defined as polyhydroxy aldehydes or ketones and its derivatives
or as substances that yield one or more of these compounds on hydrolysis.
Biological importance%
(. +t provides energy to the body by oxidation reactions of simple sugars in the form
of C'
)
, &
)
' and energy in the form of AT,. "-x% Glucose$
). !ome carbohydrates provide mechanical support or present as a cell wall structural
component. !uch as cellulose in case of plants, chitin in case of fungal cell wall
and insect integuments.
.. Certain carbohydrates act a catalysts or promoters in oxidation of food stuffs. "-x%
Lactose$
/. some carbohydrates act as a precursor or substrates for the synthesis of other
Biomolecules such as fatty acids* lipids, proteins, etc.,
0. Vit C. or Ascorbic acid is a sugar
1. some carbohydrates serve to lubricate the s2eletal 3oints "ex% Hyaluronic acid$
4. +t acts as detoxifying agents by combining with some toxic substances and bacterial
byproducts "ex% Glucuronic Acid$.
5. !ome act as drugs or help in carriage of drugs to target site. "-x% Glucosides is an
important drug for heart diseases$.
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volume 28

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6. !ome act as an osmoregulator, hence protect the cell from various stresses. !uch
as sucrose, maltose etc.,
(7. !ome involved in cell adhesions and cell to cell communication. 8lycolipids,
8lycoprotein are important con3ugate carbohydrates, these acts as receptors for
various cellular activities. !ome 8lycoprotein present as immunopolysaccharides,
which resist various microbial infection.
Classification of carbohydrates%
Based on number of sugar units carbohydrates are classified as
(. Monosaccharides.
). 'ligosaccharides.
.. ,olysaccharides.
Chart: classification of carbohydrates:


4

MONOSACCHARDES
These contain only one sugar unit and they can not be further hydrolyzed into
simple substances. The empirical formula is C
n
"&
)
'$
n
. The Monosaccharides are having
names with suffix ose. Monosaccharides are further classified based on
a$ ature of carbonyl carbon atom present in the structure.
b$ Based on number of carbon atom the structure possesses.
a$ Monosaccharides have two family based on nature of carbonyl carbon atom which
present in the structure.
a. +f the carbonyl carbon atom is placed at any one end of the bac2bone, it
becomes aldehyde group, such Monosaccharides are belongs to aldoses
family.
b. +f the carbonyl carbon atom is placed at any other position, then it become
2eto group, and belongs to ketoses family.

b$ The Monosaccharides also classified based on number of carbon atoms that
possesses in their structures. 9epending upon the number of carbon atoms that
possesses in their structure carbohydrates have many subgroups such as%
a. Diose% have ) carbon atoms, molecular formula is C
)
&
/
'
)
-x%
Glycoaldehyde.
b. Trioses% these have . carbon atom in their structure, and have both 2etose
and aldose family. Molecular formula is C
.
&
1
'
.
-x% Glyceraldehyde
"aldotriose$ and Dihyrodoxy acetone ":etotriose$.
c. Tetrose % have four carbon atoms, the molecular formula is C
/
&
5
'
/
-x%
rythrose, !hreose "Aldotetrose$ and rythrulose "2etotetrose$
d. !entose% &ave five carbon atoms. Molecular formula is C
0
&
(7
'
0
-x% "ibose,
xylose "aldopentose$ and ribulose and xylulose "2etopentose$
volume 28

5

e. He"oses% &ave six carbon atoms. The molecular formula is C
1
&
()
'
1
-x%
Glucose, #annose and Galactose "aldohexoses$ and $ructose ":etohexoses$.
f. He#toses% have seven carbon atoms. The molecular formula is C
4
&
(/
'
4
-x%
sedoheptose "aldoheptose$ and sedoheptulose "2etoheptoses$

Structure of various monosaccharides
Aldose family


6

etose family

STRCT$RE O% MONOSACCHARDES OR %OR$M$A&TONS O% MONOSACCHARDES
(E"' (l)cose)
+n nature, the Monosaccharides present in different form. The monosaccharides
may be represented in following structural conformations, they are%
A. !traight chain structure or open chain structure or ;ischer conformation.
B. Cyclic structure or ring structure.
C. Boat and chair conformations.
volume 28

7

A* Strai+ht Chain str)ct)re or o#en chain str)ct)re*
a. ;itting and Baeyer first time proposed a straight chain structure, according
to tem, monosaccharides contains an aldehyde group at one end, C&
)
'&
group at the other end and four C&'& groups in between "with respect to
&exoses$.
b. ;ischer proposed another straight chain structure. &ence that open chain
structure also called as a ;ischer Conformation or pro3ection formulae.
According to him, in 8lucose or aldoses aldehyde group is placed at one end
and the remaining carbon atoms are arranged one behind the other. The
last carbon atom contains two hydrogen atoms and one hydroxyl group. The
remaining carbon atoms contain one hydrogen "< &$ on one side and one
hydroxyl "<'&$ group on the other side. The carbon atoms are numbered
from the aldehyde group.
c. The characteristic feature of straight chain structure is the presence of free
aldehyde group "with reference to 8lucose structure$.

B. Cyclic Str)ct)re or Rin+ str)ct)re%
a. +n this structure, the atoms are arranged in the form of a ring.
b. &aworth "(6)6$, devised the ring structure, hence ring structure also
referred as &aworth=s pro3ection formulae. &ere the sugars will exist in the
two types of rings pyranose and furanose ring.
c. $uranose rin%%


8

i. +t is a 0 membered ring "pentagonal ring$, it resembles the ring of a
compound called as furan hence name the same with suffix >ose.
ii. This is formed by hemiacetal ring formation ta2en place from
aldehyde or first C< atom with that of hydroxyl group of /
th
Carbon
atom.
iii. ;uranose ring is / carbon atoms and one oxygen atom? hence it is a 0
membered ring.
d. &yranose rin%%
i. +t is a 1<membered ring. "&exagonal ring$, it resembles the ring of a
compound called as pyran.
ii. !ugars containing the pyran ring are called as pyranose sugars.
iii. +t is more commonly present structure in &exoses.
iv. +t is formed by the hemiacetal ring formed between the aldehyde
group and with that of hydroxyl group of the 0
th
Carbon atom? hence
the pyranose ring is having the 0 carbon atoms and one oxygen atom.

volume 28

9

e. The numbering of the carbon atoms is made from the anomeric carbon
atom, and numbering must be in cloc2 wise direction.
f. "ules for Ha'orth structure%
i. ,yran ring or furan ring structure is made each corner indicates the
carbon atom
ii. The atoms or group of atoms present in the right side should be
drawn below the plane and those present in the left side should be
drawn above the plane "except carbon 0 in case of pyranose ring and
/ in case of furanose ring$ through vertical lines drawn at the corner
of the ring.
iii. The terminal group "C&
)
'& or other group$ of the straight chain
structure is attached to the upper end of the plane through vertical
line.
g. The characteristic feature of the cyclic structure is the absence of the free
aldehyde group in 8lucose.
C* Boat and chair confi+)ration'
a. Conformation refers to @the spatial arran%ement of substituent %roups that
are free to assume different positions in space, 'ithout breakin% any
bonds, because of freedom of bond rotationA.
b. The six membered rings cannot be a planar because of its tetrahedral
geometry and its saturated carbon atoms. +nstead, pyranose rings adopt
chair and boat conformations.
c. The substituents of carbon ring are arranged in axial and e(uatorial
orientations.
d. Axial bonds are nearly perpendicular to the average plane of the ring.
e. -Buatorial bonds are almost parallel to the planar ring.
f. Axial substituents are present above or below the average plane of the ring
sterically hinder each other if they emerge on the same side of the ring. By
contrast the eBuatorial groups are at the periphery and are less crowded.


10

g. The chair form of C< 9< glucopyranose predominates, because of all axial
positions are occupied by hydrogen atoms. The bul2ier > '& and > C&
)
'&
groups emerge at the less hindered periphery.
h. Boat form is highly disfavor because of its hindered steriochemical
structure.

STEREOCHEMSTRY'
ASYMMETRC CARBON ATOM OR CHRA& CARBON ATOM
The carbon atom is surrounded by a four different atoms or group of atoms are
called as asymmetric carbon atom or chiral carbon and the compound is called is
asymmetric compound. The number of asymmetric carbon atom in a carbohydrate
mainly in monosaccharides are determined by the vant Hoff)s rule of Dn=, it states that
the probable number of isomers obtained is by the number of asymmetric carbon
present. The mathematical expression is number of probable isomers obtained is )
n
.
Ehere n is the number of asymmetric carbon atoms that compound possesses.
Stereoiso,ers' -!hese are isomers are havin% same molecular formulae but
different in spatial arran%ement of atoms or %roup of atomsA.
+f the hydroxyl group on the highest asymmetric carbon atom or chiral carbon atom
or on the pen ultimate carbon atom is on the right hand side, than the compound will
volume 28

11

belong to 9 < series. +f the hydroxyl group is on left side, than the compound will
belong to F > series. The 9 and F< series are !tereoisomers.
$i%: D and L * forms are %iven belo' 'ith respect to Glyceraldehyde and Glucose.

The 9 and F > isomers are mirror images to each other. The !tereoisomers are also
called as @!"A#I$%$&'(SA. 8lucose with four asymmetric carbon atoms will have
)/, i.e., (1 isomers of 5 9 > series and 5 F< series. +t is seen during the open chain
form but, there are .) isomers are elucidated, this concept was explained by the
cyclization or ring structure of the 8lucose.

!'I%!&S:
@!'o su%ars 'hich differ from one another only in the confi%uration around one
specific carbon apart from carbonyl carbon atom are called pimersA.
-x% 9< 8lucose and 9< Mannose is C<) epimers with respect to carbon atom number ).
!imilarly 9<8lucose and 9<8alactose are C</ epimers with respect to carbon atom
number /. Ehere the hydroxyl group on carbon / is left hand side in 8alactose and it is
right hand side placed in 8lucose. The process of interconversion from one -pimer to
another li2e for example from 8alactose to 8lucose is called as @epimeri+ationA.


12

$i%: C,- and C, . epimers

C)C*I+A#I$" $, %$"$SACC(A&ID!S $& (!%IAC!#)*A#I$" &!AC#I$":
+n monosaccharides mainly from pentoses onwards, cyclization reaction will occur in
solution. 8lucose under cyclization of chain by hemiacetylation reaction. The
hemiacetylation reaction is a condensation reaction occurred with in the compound
between the carbonyl group such as aldehyde with that of hydroxyl groups. By removal of
a molecule of water, the oxygen valence forms a bridge between first carbon with that of
hydroxyl bearing carbon atom "in case of 8lucose, it may be /
th
or 0
th
carbon atom that
may participate in hemiacetalization reaction$. The newly formed oxygen bridge is called
as hemiacetal lin2age or bond or ring. This ma2es the compound to go for a cyclic
structure.
+f the hemiacetal ring is formed between (
st
and 0
th
carbon atom it forms 1 >membered
ring called as pyran ring, therefore the monosaccharides which possesses this structure are
called pyranose structure. But if the ring formed by participation of (
st
and /
th
carbon
atom it forms a 0 >membered ring of furan hence the carbohydrates which shows this
structure are called as furanose.
By the hemiacetal ring formation, there is a new asymmetric carbon atom was created
at the carbonyl or (
st
carbon atom "in case of aldoses$, this newly formed carbon atom is
called as anomeric carbon atom. This also shows some isomeric property.

volume 28

13

$'#ICA* AC#I-I#).$'#ICA* IS$%!&S:
Ehen a beam of plane polarized light is passed through a solution of
carbohydrates, if the compound rotate the plane polarized light toward the right or cloc2
wise direction, it is said to be dextrorotatory "denoted asDd= or DG=$, if the plane polarized
light rotated by the compound towards the left or counter cloc2 wise* anticloc2wise
direction then it is said to be laevorotatory in nature. "9enoted as Dl= or D<D$.
A"$%!&S:
Carbohydrates that differ only in their configuration around the carbonyl carbon
atom or newly formed asymmetric or chiral carbon atom are called as Anomers. The


14

newly formed asymmetric carbon atom after hemiacetylation reaction is called anomeric
carbon atom.
H<9<glucose and C<9<glucose are anomeric forms of glucose. +n the H<9<glucose the
hydroxyl group on anomeric carbon atom is on right side, whereas in C<9<glucose the
hydroxyl group on left hand side.
+n &aworth= structure, the '& below the plane of the ring is called as H > side, and
above the plane of the ring is called as C > side.
$i%: !he t'o anomeric forms of %lucose are depicted belo':

!RO!ERTES O% MONOSACCHARDES%
a$ Colour' colorless.
b$ Shape% crystalline.
c$ Solubility' soluble in water.
d$ #aste' sweet taste.
e$ $ptical activity% exhibited both in d or G and l or < form
f/ %utarotation: Mutarotation is defined as @the chan%e in specific rotation of
optically active solution from one form to another 'ithout chan%e in their
propertyA.
Ehen glucose is dissolved in water, the optical rotation of the solution is
gradually changes and attains the eBuilibrium value. This change in optical
activity is called Mutarotation.
volume 28

15

"eason% the Mutarotation occurs due the cyclization of open chain of glucose
into H or C > form with eBual probability. The H I C both will have different
optical activity. The H form of glucose is having optical activity of about
G(().)
7
and C form is of G(6
7
, and they are not mirror images, they differ in
configuration only in and around the carbonyl carbon atom. The eBuilibrium
state will have the value of about G0).0
7
.
Ehen a solution of H > 9 > glucose was allowed to stand, the optically
activity is falls to G0).4
7
and remain constant. !imilarly with respect to C > 9 >
glucose solution, there is an increase in the optically to attain G0).4
7
.
This is
due to interconversion of optical activity. This interconversion is called as
Mutarotation.

The value of Mutarotation for H > 9 > glucose is G06.0
7
. The value obtained
by subtracting the final value from the original value. J"G(().)
7
$ > "G0).4
7
$K.
!imilarly freshly prepared solution of C > 9< glucose has a rotation value of G(6
7
.
+t also gradually increases and reaches the final value of G0).4
7
.


16

%/ Chemical properties%
(. 0lucoside formation%
Ehen glucose reacts with methyl alcohol in the presence of
hydrogen chloride gas to give 8lucosides. 8lucosides are formed due to the
reaction of alcohol with the glucosidic hydroxyl group of monosaccharides.

(l)cose . ,ethyl alcohol /////////// 0 ,ethyl +l)coside*

12 !sterification:
8lucose reacts with 0 molecules of acetic anhydride to form esters.
The ability of sugars to form esters indicates the presence of alcohol
groups. As glucose yield penta acetate derivative on acetylation, hence it
indicates the presence of 0 hydroxyl groups in glucose.

.. &eduction%
Monosaccharides can be reduced by various reducing agents. The
reduction is due to the presence of aldehyde or 2etone group in a
compound, on reduction it yields alcohols.
volume 28

17

Ehen glucose is treated with reducing agents such as sodium
amalgam, it produced sorbitol, similarly mannose yields mannitol, 8alactose
yields dulcitol and fructose yields both sorbitol and mannitol.

/. &educing agents%
Monosaccharides act as best reducing agents. They readily reduce
oxidizing agents such as feerycyanide, hydrogen peroxide or cupric ion. +n
such reactions, the sugars oxidized at the carbonyl group and the oxidizing
agent becomes reduced.
Monosaccharides or sugars capable of reducing oxidizing agents are
called reducing sugars. This is very useful in analysis of sugars. By
measuring the amount of an oxidizing agent that is reduced by a solution of
sugar, it is possible to estimate the concentration of sugar. 8lucose
reduces #ollen3s reagent4 ,ehling3s solution4 Benedict3s reagents etc.
By oxidation the glucose will produce different sugar acids.
(. Aldonic acids% the first carbon atom is oxidized to carboxyl
group only, others are unaffected. Glucose is producing
%luconic acids. +t is a monocarboxyl acid sugar compound.
). 5ronic acid: whereby the terminal carbon atom is oxidized to
carboxyl group only. The first carbon atom that is aldehydic


18

group and the rest of molecular structure is unaffected.
Glucose gets converted to Glucuronic acid. +t is a monocarboxyl
acid sugar
.. Aldaric or saccharic acids: whereby both first and last carbon
atoms, that is aldehydic and terminal carbon atom carries
alcoholic groups are oxidized to carboxyl groups. +t is a
dicarboxylic acid sugar compound
Galactose undergoes oxidation to form a dicarboxylic acid, mucic acid. This
reaction is very important for identification of Galactose.

0. ,ormation of $sa6one%
Most of the reducing sugars are easily distinguished by 'sazone test.
These osazones have characteristic structures, melting point and
precipitation time and show different crystalline structures. Three
molecules of phenylhydrazine is reBuired for the production of one
molecule of osazone. Leaction with phenylhydrazine involves only two
carbon atoms, namely the carbonyl carbon atom "aldehyde or 2etone$ and
the ad3acent one. ;irst of all one molecule of phenylhydrazine reacts with
one molecule of aldose or 2etose to form a molecule of hydrazone. Eith
the second molecule of phenylhydrazine, the hydrazone is oxidized to
aldohydrazone and the phenylhydrazine itself is reduced to aniline and
ammonia. ;inally, a third molecule of phenylhydrazine reacts with the
aldohydrazone to produce osazone. :etoses are also produces osazone in
the same manner.
8lucose, fructose and mannose give the needle shaped osazones
whereas maltose gives sunflower and lactose gives cotton ball or puff ball
volume 28

19

shaped osazones. The yellow osazone produced are microscopically
observed.

Maltose lactose glucose
1. Aldoses and 2etoses are reacts with hydroxylamine and produces oximes.
8lucose produces glucoxime with hydroxylamine.
4. !ugars are treated with hydrogen cyanide and produces cyanohydrin. This
reaction produces new asymmetric carbon atom. Therefore this test is used
in 0illani synthesis of sugars, by increasing the length of the carbon chain in
sugars. 0illani synthesis involved
a. ;ormation of cyanohydrin.
b. Cyanohydrin is hydrolyzed to produce carboxylic acid.
c. Carboxylic acids then converted to M<lactone by lactonization.


20

d. Factones are reduced to aldose, containing one added carbon atom.
5. some other derived sugars
a. Deoxy ribose% main component of 9A, derived from pentose sugar,
ribose. Ehere oxygen is removed in the ribose sugar at )
nd
carbon
atom position. &ence it is a )<deoxy ribose sugar.

b. Aminosu%ars: Glucosamine and Galactosamine are naturally
occurring. The aminosugars are acetylated and acetylated
aminosugars are main monomer for many polysaccharides such as
hyaluronic acid, chitin, peptido%lycan etc.,

c. phosphorylation of Hexoses% the formation of phosphoric acid
derivatives have vital role in energy production in the living system
and it is a important step involved in many carbohydrate metabolism
such as glycolysis, :reb=s cycle, gluconeogenesis etc.,
volume 28

21

O&(OSACCHARDES' (oligo 7 few8 saccharides 7 sugar)
(. 'ligosaccharides are sugar by hydrolysis yield ) to (7 monosaccharide units.
). They are sweet in taste, soluble in water.
.. The general formula for oligosaccharide is C
n
"&
)
'$
n<(
. The common
oligosaccharides are sucrose, maltose and lactose.
/. Ehen oligosaccharides contain two sugar units, then it is called as disaccharides, if
it is made up of three, then it is trisaccharides and so on.
0. +n oligosaccharides, monosaccharides are lin2ed by 8lycosidic bonds.
1. 0lycosidic *inkage% 8lycosidic lin2age is a bond formed between monomers,
which lin2 one carbohydrate with that of other carbohydrate. The bond is formed
by the removal of a molecule of water "condensation reaction$. 9uring the bond
formation then hydroxyl group form one monosaccharide is eliminated along with
the hydrogen atom of the other monosaccharide unit. The remaining oxygen atom
forms the 8lycosidic bond between the participated carbon atoms. The eliminated


22

>'& and >& atoms combines and a water molecule is formed. Ehen carbohydrates
are lin2ed, the 8lycosidic bond is formed by oxygen atom, this bond is called '<
glycosidic bond
+f two monosaccharides are involved in the bond formation, one molecule of
water is released, which results in disaccharide. +f two water molecules are
released then the sugar formed is trisaccharides.

4. Classification of oli%osaccharides% oligosaccharides arte classified based on the
number of monosaccharides units that present. !o they are classified as
disaccharides "made<up of two sugar units$ , trisaccharides "made<up of three sugar
units$, tetrasaccahrides "made<up of four sugar units$ etc.,
DSACCHARDES'
9isaccharides yield ) molecules of sugar units on hydrolysis. The disaccharides are
further classified based on the reducing property as reducing sugars and non< reducing
sugars.
1* S$CROSE'
o +t is a disaccharide.
o Commonly called as cane sugar or table sugar.
o +t is common sugar present in all photosynthetic plants.
o !ucrose on hydrolysis yield H < 9 > glucose and C > 9< fructose.
o !ucrose also 2nown as invert sugar, since, the components of sucrose is
H < 9 > glucose and C > 9 < fructose. +n which H < 9 > glucose has
dextrorotatory "G or d$ whereas C > 9< fructose has laevorotatory "< or l$.
Ehen in a sucrose solution, there is inversion of sign of rotation. &ence
the sucrose is called invert sugar.
o The glucose and fructose units get lin2ed with each other by H "( )$ C
lin2age.
o &roperties% +t is a white crystalline solid, soluble in water and with a
melting point of (57
7
C, when heated above its melting point it forms a
brown substance called as caramel. +t is dextrorotary and has a specific
volume 28

23

rotation of G11.4
7
. +t is non<reducing sugar since, no free anomeric
carbon atoms they are involved in the bond formation.
o +t does not exhibit Mutarotation.
o +nvertase enzyme hydrolyzes sucrose.
2* &ACTOSE'
o The lactose is purely of animal origin.
o Commonly called as mil2 sugar.
o 'n hydrolysis yields C > 9< 8alactose and C<9<glucose.
o &roperties% Fess soluble in water and less sweet than the sucrose, it is
white, crystalline solid with melting point of )7.
7
C and it is dextrorotary
"H form has G67
7
and C form has G.0
7
$. +t is a reducing sugar and exhibits
Mutarotation due to free anomeric or aldehydic group.
o Factase enzyme hydrolyses the lactose to glucose and 8alactose.
o The 8alactose and glucose are bonded by C "( /$ C 8lycosidic lin2age.
o The intestine of mil2 suc2ing infants have lactase enzyme, which
converts lactose to glucose and 8alactose, these are then absorbed by
the body. -xcess of lactose will leads to indigestion problems such as
diarrhea, abnormal intestinal flow etc.
3* MA&TOSE'
o +t is a disaccharide commonly called as malt sugar "malt from sprouting
barley is the maltose source$.
o &roperties% it is white crystalline solid, with melting point (17 > (107C,
soluble in water and is dextrorotary. +t is a reducing sugar. +t reduces
$ehlin%)s solution and !ollen)s "ea%ent. This indicates the presence of
free aldehyde group or anomeric carbon atom.
o +t is produced by partial digestion of starch by 1 * amylase "or diastase$.
o Maltose is made up of two H < 9< glucose units.
o The lin2age in maltose is found to be H "( /$ lin2age.
o #altase enzyme catalyzes the maltose and produces glucose units.


24

Summary of three disaccharides
"ame $ccurrence Constituents *inkage
involved
0roups
involved in
linkage
'roperties (ydrolysis
!ucrose ,lant origin H< 9< glucose
and C < 9<
fructose
H"()$C 8lycosidic '&
on C( and
8lycosidic '&
on C)
9extrorotary,
nonreducing, white
crystalline, does not
exhibit Mutarotation,
does not form
osazones
By invertase
enzyme yield
eBuimolar of
glucose and
fructose
Factose Animal origin
found in mil2
C < 9<
8alactose and
H< 9< glucose
C "( /$H 8lycosidic '&
group on C( and
alcoholic group
on C/
9extrorotary,
reducing, white
crystalline, exhibit
Mutarotation, form
lactosazones "cotton
ball or puff shaped
crystals$
By lactase
enzymatic action
yield eBuimolar
concentration of
8alactose and
glucose
Maltose 9oes not
occur
predominantl
y in nature,
malt from
sporulating
barely seeds
H< 9< glucose
and H< 9<
glucose
H "( /$H 8lycosidic '&
group on C( and
alcoholic group
on C/
9extrorotary,
reducing, white
crystalline, exhibit
Mutarotation, form
maltosazones
"sunflower shaped$
Nields identical
units of gluoses on
hydrolysis of
maltase or diastase
enzyme.

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25

!O&YSACCHARDES (poly 7 many8 saccharum 7 sugar units)
,olysaccharides are @hi%h molecular 'ei%ht, amorphous and insoluble non,su%ars
does not havin% any s'eet taste, %ives more than 23 monosaccharides molecules on
hydrolysis and does not exhibit any property of aldehyde or ketoneA. They may be also
regarded as the polymeric anhydrides of simple sugars. ,olysaccharides also called as
@%lycanA.
Classification of polysaccharides% polysaccharides are classified based on the chemical
composition*type of the monosaccharides that polysaccharide made up or based on the
functions%
Classification of polysaccharides based on the type of monosaccharides : there are
two types as?
o Homopolysaccharide% made up of similar or single type of monosaccharides.
-x.% glucose, !tarch chitin etc.,
o Heteopolysaccharides% are composed of mixture of monosaccharides. -x%
&yaluronic acid, Chondritin, heparin, agar > agar etc.,
Classification of polysaccharides based on their biolo%ical functions%
o 4tructural polysaccharides% these polysaccharides are involved in the
structure of several biological membranes and cell walls. x: chitin,
cellulose, hemicelluloses etc.,
o 4tora%e polysaccharides% polysaccharides are involved in storage of energy
as reserve food materials within the cell "or in some cell organelles$. x:
starch and %lyco%en
1* STARCH'
+t is a homopolysaccharide, on hydrolysis yields glucose units? hence it is called
@%lucanA.
+t is the reserve food material in plants. ,redominantly present in tubers such
as potatoes, legumes, other vegetables etc.,
,roperties% it is a soft, white amorphous powder and a tasteless substance. +t is
insoluble in cold water, ether and ethanol at ordinary temperature. The
specific rotation of starch is around G(61
7
.


26

!tarch on partial hydrolysis yields dextrin. 9extrin used as an adhesive and also
a feed for infants because of easy digestibility.
+t is highly hydrated since they contain exposed hydroxyl groups. &ence it forms
granules with hot water, forms turbid colloidal solutions.
H > amylase enzyme hydrolysis the starch and produces glucose units.
The two components of the starch that is amylose and amyl pectin.
Amylose%
o +t is a homopolysaccharide with a molecular weight of (7,777 to 07,777.
o +t is water soluble, it is linear chain component of starch component
made up of H "( /$ lin2age.
o The amylose chain is in the form of H helix? each turn is made up of 1
units.
o Amylase enzyme converts amylose into maltose.
o Amylose may be considered as an anhydride of H > 9< glucose units.
o +t gives intense blue colour with iodine.

Amylopectin%
o +t is a homopolysacchride and a component of starch, with high
molecular weight.
o +t is also called as C > amylose or isoamylose.
o +t is a branched chain polysaccharide in starch.
o +t is insoluble in water.
o +t gives isomaltose during incomplete hydrolysis.
o +t is made<up of glucose units.
volume 28

27

o +t has H "( /$ glycosidic lin2age and H "( 1$ 8lycosidic lin2age. The
glucose units have . points of attachment to serve as branching point.
The branching of chain occurred by H "( 1$ 8lycosidic lin2age.
o The average chain length in Amylopectin is between )7<)/ glucose units.
o +t is laminated, highly branched in structure.
o +t gives purple colour with iodine.
o +t is not easily dispersed in water.

2* (&YCO(EN%
+t is a ma3or reserve food material in animals and it is often called as @animal
starchA. +t is stored in the muscles and liver "nearly 4O of the wet weight$. The
particles of glycogen stored in liver are having much smaller size when
compared to starch.
+t is a homopolysaccharide, since it gives glucose units on complete hydrolysis.
8lycogen is a branched chain polysaccharide, and resembles Amylopectin rather
than amylose but it has branching point at every (7<() glucose units. &ence
the molecule is highly branched and more compact.
+t consists of both H "( /$ glycosidic lin2age and H "( 1$ 8lycosidic lin2age
and the branching of chain occurred by H "( 1$ 8lycosidic lin2age. The


28

external branching of glycogen molecules contain 1 to 4 glucose units where are
as internal branching contain only . glucose units.
The molecular weight of glycogen is around ( to ) x (7
4
.
,roperty% it is a white powder, and more soluble in water than Amylopectin.
&ence it forms suspension immediately in cold water. 8lycogen precipitated
from aBueous solutions by additions of ethanol and fairly soluble in al2ali. +t is a
non<reducing sugar and gives red color with iodine. The red colour disappears
on boiling and reappears on cooling.
The liver glycogen supplies glucose to all cells and tissues. Ehen the blood
sugar exceeds (O, the excess glucose is transported to the liver and converted
into glycogen "this process is called as %lyco%enesis$. +f the blood glucose level
is below (O, then the liver glycogen is bro2en into simpler units of glucose and
released into the blood stream "by the process %lyco%enolysis$.
8lycogen resembles the Amylopectin of starch chemically but differs from it in
molecular weight and degree of branching.

3* CHTN%
+t is an important homopolysaccharide, and second abundant polysaccharide on
earth "first is cellulose$. The exos2eletons of arthropods are mainly composed
of chitin.
+t is predominantly present in the arthropod group and present in cell wall of
fungus.
volume 28

29

Chitin is hydrolyzed by the chitinase enzyme. 'n complete hydrolysis, chitin is
decomposed into 5, acetyl%lucosamine.
The 5,acetyl %lucosamine is lin2ed by 6 72 ./ glycosidic lin2age. +t is related
to cellulose, the alcoholic "< '&$ group on carbon atom of ) of 6 * D * %lucose
units is replaced by < acetyl aminogroup.
+t is indigestible by vertebrate animals because of 6 72 ./ glycosidic lin2age.


30

'late 9: 'lant 'olysaccharides

volume 28

31

!late 2' iso,eric #ro#erties of ,onosaccharides


32

E"tra ca#s)le 1' %)nctions of Carbohydrates
Carbohydrates have six ma3or functions within the body%
(. ,roviding energy and regulation of blood glucose
). !paring the use of proteins for energy
.. Brea2down of fatty acids and preventing 2etosis
/. Biological recognition processes
0. ;lavor and !weeteners
1. 9ietary fiber
1* !ro4idin+ ener+y and re+)latin+ blood +l)cose
8lucose is the only sugar used by the body to provide energy for its tissues.
Therefore, all digestible polysaccharides, disaccharides, and monosaccharides must
eventually be converted into glucose or a metabolite of glucose by various liver enzymes.
Because of its significant importance to proper cellular function, blood glucose levels must
be 2ept relatively constant.
Among the enormous metabolic activities the liver performs, it also includes
regulating the level of blood glucose. 9uring periods of food consumption, pancreatic beta
cells sense the rise in blood glucose and begin to secrete the hormone insulin. +nsulin binds
to many cells in the body having appropriate receptors for the peptide hormone and
causes a general upta2e in cellular glucose. +n the liver, insulin causes the upta2e of
glucose as well as the synthesis of glycogen, a glucose storage polymer. +n this way, the
liver is able to remove excessive levels of blood glucose through the action of insulin.
+n contrast, the hormone glucagons is secreted into the bloodstream by pancreatic
alpha cells upon sensing falling levels of blood glucose. Ppon binding to targeted cells such
as s2eletal muscle and brain cells, glucagon acts to decrease the amount of glucose in the
bloodstream. This hormone inhibits the upta2e of glucose by muscle and other cells and
promotes the brea2down of glycogen in the liver in order to release glucose into the
blood. 8lucagon also promotes gluconeogenesis, a process involving the synthesis of
glucose from amino acid precursors. Through the effects of both glucagon and insulin,
blood glucose can usually be regulated in concentrations between 47 and ((0mg*(77 ml of
blood.
'ther hormones of importance in glucose regulation are epinephrine and cortisol.
Both hormones are secreted from the adrenal glands, however, epinephrine mimics the
volume 28

33

effects of glucagon while cortisol mobilizes glucose during periods of emotional stress or
exercise.
9espite the liverQs uniBue ability to maintain homeostatic levels of blood glucose, it
only stores enough for a twenty<four hour period of fasting. After twenty four hours, the
tissues in the body that preferentially rely on glucose, particularly the brain and s2eletal
muscle, must see2 an alternative energy source. 9uring fasting periods, when the insulin
to glucagons ratio is low, adipose tissue begins to release fatty acids into the bloodstream.
;atty acids are long hydrocarbon chains consisting of single carboxylic acid group and are
not very soluble in water. !2eletal muscle begins to use fatty acids for energy during
resting conditions? however, the brain cannot afford the same luxury. ;atty acids are too
long and bul2y to cross the blood<brain barrier. Therefore, proteins from various body
tissues are bro2en down into amino acids and used by the liver to produce glucose for the
brain and muscle. This process is 2nown as gluconeogenesis or Rthe production of new
glucose.R +f fasting is prolonged for more than a day, the body enters a state called
2etosis. :etosis comes from the root word 2etones and indicates a carbon atom with two
side groups bonded to an oxygen atom. :etones are produced when there is no longer
enough oxaloacetate in the mitochondria of cells to condense with acetyl CoA formed
from fatty acids. 'xaloacetate is a four<carbon compound that begins the first reaction of
the :rebs Cycle, a cycle containing a series of reactions that produces high<energy species
to eventually be used to produce energy for the cell. !ince oxaloacetate is formed from
pyruvate "a metabolite of glucose$, a certain level of carbohydrate is reBuired in order to
burn fats. 'therwise, fatty acids cannot be completely bro2en down and 2etones will be
produced.
2* S#arin+ !rotein and !re4entin+ 5etosis
!o why are carbohydrates important if the body can use other carbon compounds
such as fatty acids and 2etones as energyS ;irst of all, maintaining a regular inta2e of
carbohydrates will prevent protein from being used as an energy source. 8luconeogenesis
will slow down and amino acids will be freed for the biosyntheses of enzymes, antibodies,
receptors and other important proteins. ;urthermore, an adeBuate amount of
carbohydrates will prevent the degradation of s2eletal muscle and other tissues such as
the heart, liver, and 2idneys. Most importantly, 2etosis will be prevented. Although the
brain will adapt to using 2etones as a fuel, it preferentially uses carbohydrates and
reBuires a minimum level of glucose circulating in the blood in order to function properly.


34

Before the adaptation process occurs, lower blood glucose levels may cause headaches in
some individuals. To prevent these 2etotic symptoms, it is recommended that the average
person consume at least 07 to (77g of carbohydrates per day.
Although the processes of protein degradation and 2etosis can create problems of
their own during prolonged fasting, they are adaptive mechanisms during glucose
shortages. +n summary, the first priority of metabolism during a prolonged fast is to
provide enough glucose for the brain and other organs that dependent upon it for energy
in order to spare proteins for other cellular functions. The next priority of the body is to
shift the use of fuel from glucose to fatty acids and 2etone bodies. ;rom then on, 2etones
become more and more important as a source of fuel while fatty acids and glucose
become less important.
3* %la4or and S6eeteners
A less important function of carbohydrates is to provide sweetness to foods.
Leceptors located at the tip of the tongue bind to tiny bits of carbohydrates and send
what humans perceive as a RsweetR signal to the brain. &owever, different sugars vary in
sweetness. ;or example, fructose is almost twice as sweet as sucrose and sucrose is
approximately .7O sweeter than glucose.
!weeteners can be classified as either nutritive or alternative. utritive
sweeteners have all been mentioned before and include sucrose, glucose, fructose, high
fructose corn syrup, and lactose. These types of sweeteners not only impart flavor to the
food, but can also be metabolized for energy. +n contrast, alternative sweeteners provide
no food energy and include saccharin, cyclamate, aspartame, and acesulfame. Controversy
over saccharin and cyclamate as artificial sweeteners still exists but aspartame and
acesulfame are used extensively in many foods in the Pnited !tates. Aspartame and
acesulfame are both hundreds of times sweeter than sucrose but only acesulfame is able
to be used in ba2ed goods since it is much more stable than aspartame when heated.
7* Dietary %iber
9ietary fibers such as cellulose, hemicellulose, pectin, gum and mucilage are
important carbohydrates for several reasons. !oluble dietary fibers li2e pectin, gum and
mucilage pass undigested through the small intestine and are degraded into fatty acids
and gases by the large intestine. The fatty acids produced in this way can either be used
as a fuel for the large intestine or be absorbed into the bloodstream. Therefore, dietary
fiber is essential for proper intestinal health.
volume 28

35

+n general, the consumption of soluble and insoluble fiber ma2es the elimination of
waste much easier. !ince dietary fiber is both indigestible and an attractant of water,
stools become large and soft. As a result, feces can be expelled with less pressure.
&owever, not enough fiber consumption will change the constitution of the stool and
increase the amount of force reBuired during defecation. -xcessive pressure during the
elimination of waste can force places in the large intestine wall out from between bands
of smooth muscle to produce small pouches called diverticula. &emorrhoids may also
result from unnecessary strain during defecation.
The disease of having many diverticula in the large intestine is 2nown as
diverticulosis. Although diverticula is often asymptomatic, food particles become trapped
in their folds and bacteria begin to metabolize the particles into acids and gases.
-ventually, the diverticula may become inflamed, a condition 2nown as diverticulitis. To
combat the disease, antibiotics are administered to the patient to destroy the bacteria
while the inta2e of fiber in the diet is decreased until the inflammation has subsided.
'nce the inflammation has been reduced, a high fiber diet is begun to prevent a relapse.
Besides the prevention of intestinal disease, diets high in fiber have other health
benefits. &igh fiber inta2e reduces the ris2 of developing obesity by increasing the bul2 of
a meal without yielding much energy. An expanded stomach leads to satisfaction despite
the fact that the caloric inta2e has decreased.
Beyond dieters, diabetics can also benefit from consuming a regular amount of
dietary fiber. 'nce in the intestine, it slows the absorption of glucose to prevent a sudden
increase in blood glucose levels. A relatively high inta2e of fiber will also decrease the
absorption of cholesterol, a compound that is thought to contribute to atherosclerosis or
scarring of the arteries. !erum cholesterol may be further reduced by a reduction in the
release of insulin after meals. !ince insulin is 2nown to promote cholesterol synthesis in
the liver, a reduction in the absorption of glucose after meals through the consumption of
fiber can help to control serum cholesterol levels. ;urthermore, dietary fiber inta2e may
help prevent colon cancer by diluting potential carcinogens through increased water
retention, binding carcinogens to the fiber itself and speeding the passage of food through
the intestinal tract so that cancer<causing agents have less time to act.


36

8* Biolo+ical Reco+nition !rocesses
Carbohydrates not only serve nutritional functions, but are also thought to play
important roles in cellular recognition processes. ;or example, many immunoglobulins
"antibodies$ and peptide hormones contain glycoprotein seBuences. These seBuences are
composed of amino acids lin2ed to carbohydrates. 9uring the course of many hours or
days, the carbohydrate polymer lin2ed to the rest of the protein may be cleaved by
circulating enzymes or be degraded spontaneously. The liver can recognize differences in
length and may internalize the protein in order to begin its own degradation. +n this way,
carbohydrates may mar2 the passage of time for proteins.

,ootnote 9: Red)cin+ #otential
The anomeric carbon atoms provide sugars with their chemical reducing potential.
9isaccharides such as mannose which have a free aldehyde group are, therefore, described
as reducing sugars. !imilarly, most oligo< and polysaccharides will have a reducing end to
the molecule.
!ucrose, on the other hand, has the anomeric carbon atoms of both its constituent
sugars involved in the glycosidic bond. !ucrose is, therefore, a non<reducing sugar.
8lycosidic bonds of this type reBuire more energy for formation and, conseBuently,
release more energy when bro2en. This has implications in extracellular polysaccharide
synthesis.

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