CARBOHYDRATE
DR.ALOK PAREKH
ASSISTANT PROFESSOR,
DEPT. OF BIOCHEMISTRY,
GOVERNMENT MEDICAL COLLAGE,
SURAT
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CARBOHYDRATE CHEMISTRY
1. Definition, classification, biological
importance.
2. Monosaccharides- structure,
classification & properties.
3. Isomerism.
4. Disaccharides, Oligosaccharides-
structure, importance.
5. Polysaccharides- homo &
heteropolysaccharides, their structure
& function.
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Carbohydrates are
aldehyde or ketone
derivatives of polyhydric
alcohols.
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BIOMEDICAL IMPORTANCE
1.Knowledge of the structure & properties of
carbohydrates is essential in understanding its
role in physiological processes.
2. Glucose is the major fuel of the tissues.
3. Other carbohydrates of importance :- Glycogen for
storage; Ribose in nucleic acid; Galactose in
lactose of milk; in certain complex lipids & in
combination with protein in glycoproteins &
proteoglycans.
4. Non digestible carbohydrates serve as dietary
fibres.
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BIOMEDICAL IMPORTANCE
Diseases associated with carbohydrates:-
1. Diabetes mellitus
2. Galactosemia
3. Glycogen storage diseases
4. Lactose intolerance.
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CLASSIFICATION
1.MONOSACCHARIDES-
TRIOSES, TETROSES, PENTOSES, HEXOSES, HEPTOSES OR
OCTOSES(depending on the no. of C-atoms), ALDOSES OR
KETOSES(depending on whether aldehyde or ketone group is present)
2.DISACCHARIDES.
3.OLIGOSACCHARIDES.
4.POLYSACCHARIDES-
HOMOPOLYSACCHARIDES & HETEROPOLYSACCHARIDES.
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Carbohydrates also can combine with lipids to
form glycolipids
OR
With proteins to form glycoproteins.
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MONOSACCHARIDES
Contains only one sugar group (mono-one,
saccharin-sugar).
Cannot be hydrolysed to simpler form.
Depending on the no. of C-atoms, may be
triose, tetrose, pentose etc.
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Carbohydrates with an aldehyde as their
most oxidized functional group are called
Aldoses.
whereas those with a keto as their most
oxidized functional group are called Ketoses
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COMMON MONOSACCHARIDES
No. Of Carbon Generic name ALDOSES KETOSES
atoms
3 TRIOSE GLYCERALDEHYDE DIHYDROXY
ACETONE
PHOSPHATE
4 TETROSE ERYTHROSE ERYTHRULOSE
5 PENTOSE RIBOSE RIBULOSE
6 HEXOSE GLUCOSE FRUCTOSE
7 HEPTOSE GLUCOHEPTOSE SEDOHEPTULOSE
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DISACCHARIDES
Formed when two monosaccharides
combine together by a glycosidic
linkage with the elimination of
molecule of water.
i.e., DISACCHARIDES , ON HYDROLYSIS YIELD
TWO MOLECULES OF MONOSACCHARIDES.
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EXAMPLES OF DISACCHARIDES:-
ON HYDROLYSIS
LACTOSE:- yields one molecule of glucose
and one of galactose
MALTOSE :- yields two molecules of glucose.
SUCROSE:- yields one molecule of glucose&
one of fructose.
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OLIGOSACCHARIDES
(OLIGO-a few)
Yield 2 to 10 monosaccharide units on
hydrolysis.
Eg., MALTOTRIOSE & RAFFINOSE are
trisaccharides containing 3 glucose units.
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POLYSACCHARIDES
Yield more than 10 molecules of
monosaccharides on hydrolysis(poly-many).
Homopolysaccharides yield only one type of
monosaccharide units.
Heteropolysaccharides yield more than one
type of monosaccharides on hydrolysis.
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PROPERTIES OF MONOSACCHARIDES
FROM THE BIOMEDICAL POINT OF
VIEW, GLUCOSE IS THE MOST
IMPORTANT MONOSACCHARIDE.
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GLUCOSE IS A ALDOHEXOSE
ALDEHYDE GROUP ON C 1
HEXOSE
POLYHYDROXY COMPOUND
PRIMARY ALCOHOL GROUP ON
6TH CARBON
STRAIGHT CHAIN / OPEN CHAIN
PROJECTION FORMULA
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Important
Isomers
Epimers
Enantiomers
Anomers
D-form & L-form
d-form & l-form
α-form & β-form
(+) form & (-) form
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Isomers
Isomers are molecules that have the same
molecular formula, but have a different
arrangement of the atoms in space. (different
structures).
For example, a molecule with the formula
AB2C2, has two ways it can be drawn:
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Isomer 1
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Isomer 2
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Examples of isomers:
1. Glucose
2. Fructose
3. Galactose
4. Mannose
Same chemical formula C6 H12 O6
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EPIMERS
EPIMERS are sugars that differ in
configuration at ONLY 1 POSITION.
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EPIMERS
DIFFERS IN POSITION OF -OH GROUP AROUND A SINGLE CARBON ATOM
OTHER THAN PENULTIMATE CARBON
GLU & GAL ARE C-4 EPIMERS WHILE GLU & MANNOSE ARE C2 EPIMERS
GALACTOSE GLUCOSE MANNOSE 25
Examples of epimers :
D-glucose & D-galactose (epimeric at C4)
D-glucose & D-mannose (epimeric at C2)
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ENANTIOMERS
Non-Superimposable COMPLETE mirror
image (differ in configuration at EVERY
CHIRAL CENTER.)
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In D form the OH group on the asymmetric
carbon is on the right.
In L form the OH group is on the left side.
D-glucose and L-glucose are enantiomers:
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D-L ISOMERISM
D-GLUCOSE , D-FRUCTOSE, D-RIBOSE…
MOST NATURALLY OCCURRING SUGARS ARE D-TYPE.
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Asymmetric carbon
A carbon linked to four different atoms or
groups farthest from the carbonyl carbon
Also called Chiral carbon
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Cyclization
Less then 1%of CHO exist in an open chain
form.
Predominantly found in ring form.
involving reaction of C-5 OH group with the C-1
aldehyde group or C-2 of keto group.
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Six membered ring structures are called
Pyranoses .
five membered ring structures are called
Furanoses .
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PYRANOSE-FURANOSE ISOMERISM
α-D-GLUCOPYRANOSE & α-D-GLUCOFURANOSE
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PYRANOSE-FURANOSE ISOMERISM
α-D-FRUCTOPYRANOSE & α-D-FRUCTOFURANOSE
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Anomeric carbon
The carbonyl carbon after cyclization
becomes the anomeric carbon.
This creates α and β configuration.
In α configuration the OH is on the same of
the ring in fischer projection. In Haworths it
is on the trans side of CH2OH.
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RING STRUCTURE OF GLUCOSE
HEMI-ACETAL OR HEMI-KETAL LINKAGE
PYRANOSE RING STRUCTURE (HAWORTH
α-D-GLUCOSE.
FORMULA)
CLOSED RING STRUCTURE
GLUCOSE CAN HAVE PYRAN OR FURAN
(FISCHER FORMULA)
RING BUT PYRAN RING IS MORE
PREDOMINANT.
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ANOMERS
POSITION OF -OH GROUP ON ANOMERIC CARBON IN
RELATION TO PRIMARY ALCOHOL GROUP
β-D-GLUCOPYRANOSE α-D-GLUCOPYRANOSE44
ANOMERS
SHOWN IN PYRANOSE RING STRUCTURE
α-D-GLUCOPYRANOSE β-D-GLUCOPYRANOSE
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Terminology
SUGARS EXHIBIT VARIOUS FORMS OF
ISOMERISM
Two broad types:
STEREO-ISOMERISM & OPTICAL ISOMERISM
Stereo-isomers have same structural formula but
different spatial configuration.
No. of possible isomers of a compound is 2n
where ‘n’ is the no. of asymmetric carbon atoms.
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STEREO-ISOMERISM
1. D-L ISOMERISM.
2. PYRANOSE – FURANOSE ISOMERISM.
3. ANOMERS .
4. EPIMERS.
5. ALDOSE- KETOSE ISOMERISM.
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ALDOSE- KETOSE ISOMERISM
GLUCOSE & FRUCTOSE
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OPTICAL - ISOMERISM
BASED ON ROTATION OF PLANE POLARISED
LIGHT WHEN IT PASSES THROUGH A SOLUTION
OF A CARBOHYDRATE.
CALLED ‘d’ OR (+) WHEN plane of light TURNS
RIGHT or clockwise (dextrorotatory)
CALLED ‘ll’ OR (-) WHEN plane of light TURNS
LEFT or counter-clockwise (levorotatory)
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OPTICAL - ISOMERISM
Glucose is dextrorotatory while fructose is
levorotatory
Glucose also called dextrose & fructose also
called laevulose because of optical activity.
When equal amounts of d & l isomers are present,
activity of each isomer will cancel one another.
Such a mixture is called racemic mixture.
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