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General characteristics
-They have large number of hydroxyl groups
(polyhydroxy)
-In addition they may contain-an aldehyde group
(polyhydroxyaldehydes) or a keto group(polyhydroxyketones).
C O
-Their derivatives
may H
also
Ccontain
O nitrogen, phosphorus
or sulfur.
H COH
HYDROXYL GROUP
ALDEHYDE GROUP
KETO GROUP
Functions of Carbohydrates
1) Sources of energy, especially for brain cells and Red blood
cells.
2) Intermediates in the biosynthesis of other basic
biochemical entities (fats and proteins)
3) Associated with other entities such as glycosides, vitamins
and antibiotics)
4) Form structural tissues in plants and in microorganisms
5) Participate in biological transport, cell-cell recognition,
activation of growth factors, modulation of the immune
system
Classification of
carbohydrates
1) Monosaccharides
(monoses or glycoses)
Trioses, Tetroses, Pentoses, Hexoses
2) Oligosaccharides
Di, tri, tetra, penta, up to 9 or 10
Most important are the disaccharides
3) Polysaccharides or glycans
a)Homopolysaccharides
b) Heteropolysaccharides
Monosaccharides
-Also known as simple sugars
-Classified either by the number of carbon atoms or by the
nature of functional group-aldoses or ketoses
-Most of the carbohydrates (99%) are straight chain compounds
-D-glyceraldehyde is the simplest of the aldoses (aldotriose)
-All other sugars have the ending ose (glucose, galactose,
ribose, lactose, etc)
MONOSACCHARIDES
1-According toNOMENCLATURE
number of carbons they contain in
their backbone structuresIt is a variable prefix followed by the suffix(-ose)
(Trioses=3C), (Tetroses=4C), (Pentoses=5C),
(Hexoses=6C),(Heptoses=7C).
2- According to nature of reactive group - Aldose
sugars e.g. glyceraldehyde or a ketose sugars
e.g.dihydroxyacetone depending on the presence
of Aldehyde or keto group.
CH 2OH
C O
CH 2OH
D-Glyceraldehyde
Dihydroxyacetone.
Monosaccharides
Name
Relevant examples
Classification
3
Triose
Tetros
e
Pentos
e
5
6
9
Hexose
Nonose
Glyceraldehyde, Dihydroxyacetone
Erythrose ,Erythrulose
Ribose, Ribulose, Xylulose
Glucose, Galactose, Mannose, Fructose
Neuraminic acid
also called Sialic acid
Aldose sugars
Ketose sugars
CH 2OH
C O
CH 2OH
Dihydroxyaceton
e.
Isomerism in Monosaccharides
sugar.
D and L Isomers Of
Glyceraldehyde
D-Glyceraldehyde
L-Glyceraldehyde
Isomerism in
Monosaccharides
2) Optical Isomerism-
POLARIMETRY
Measurement of optical activity in chiral or asymmetric
molecules using plane polarized light is called Polarimetry.
The measurement of optical activity is done by an
instrument called Polarimeter.
D-Glucose +52.7
D-Fructose -92.4
D-Galactose +80.2
L-Arabinose +104.5
D-Mannose +14.2
D-Xylose +18.8
Lactose +55.4
Sucrose +66.5
Maltose +130.4
Invert sugar -19.8
Dextrin +195
Isomers differing as a result of variations in configuration of the OH and H on carbon atoms 2, 3, and 4 of glucose
are known as epimers. Biologically, the most important epimers of glucose are mannose and galactose, formed by
epimerization at carbons 2 and 4, respectively. Mannose and Galactose are not epimers of each other as they differ in
configuration around 2 carbon atoms.
Isomers of Monosaccharides
3) Epimers-
Epimers of Glucose
Isomers of Monosaccharides(Aldoses)
CH 2OH
C O
CH 2OH
Isomers of Monosaccharides
(Ketoses)
CH 2OH
C O
CH 2OH
Isomers of monosaccharides
4) Pyranose and furanose ring
structuresThe ring structures of monosaccharides are similar to the ring
structures of either pyran (a six-membered ring) or furan (a fivemembered ring)
For Glucose in solution, more than 99% is in the Pyranose form
Isomers of monosaccharides
5) AnomersThe ring structure of an aldose is a hemiacetal, since it is
formed by combination of an aldehyde and an alcohol group.
Similarly, the ring structure of a ketose is a hemiketal. The
ring can open and reclose allowing the rotation to occur
around the carbon bearing the reactive carbonyl group
yielding two possible configurations- and of the
hemiacetal and hemiketal. The carbon about which this
rotation occurs is called Anomeric carbon and the two
stereoisomers are called Anomers. Crystalline glucose is -Dglucopyranose.
Anomers
Haworth Projection
of -D-Glucose
Anomers
Anomers
Mutarotation
Isomers of Monosaccharides
6) Aldose-ketose isomerism
Fructose has the same molecular formula as glucose but differs in its
structural formula, there is a potential keto group at position 2 (the anomeric
carbon of fructose), whereas there is a potential aldehyde group at position
1, the anomeric carbon of glucose.
Glucose and Fructose are Aldose ketose isomers
Structural representation of
sugars
1) Fischer projection: straight chain representation
2) Haworth projection: simple ring in perspective
Conformational representation:
3) Chair and boat conformations
Reactions of monosaccharides
1)Osazone formation
2) Reduction
3) Oxidation
4) Action of alkali
5) Action of acid
6)Glycoside formation
7)Ester formation
Formation of osazones
Formation of osazones
Oxidation reactions
Reduction
-Either done catalytically (hydrogen and a catalyst) or enzymatically
-The resultant product is a polyol or sugar alcohol
-Glucose forms sorbitol (glucitol)
-Mannose forms mannitol
-Fructose forms a mixture of mannitol and sorbitol
-Glyceraldehyde forms glycerol
Important derivatives of
monosaccharides
1-Amino sugars
Amino Sugars
-The amino group may be condensed with active acetate
forming N-acetyl glucosamine.
-They are components of glycosaminoglycans and some
glycosphingolipids (lipids).
-N-acetyl Mannosamine- it is a component of glycoproteins and
gangliosides(Lipids) of cell membrane.
- A polymer of N-Acetyl Glucosamine is a component of chitin
- N-Acetyl Galactosamine is a component of Chondroitin
sulphate.
2-Deoxy
sugars
Deoxy Sugars
Sugar acids
3-Sugar
acids
-Are formed by the oxidation of aldehyde
C1(Aldonic acid)
-or terminal hydroxyl group at C6 of aldose
sugar(uronic acid)
-or both (saccharic) to form carboxylic group.
-Glucuronic and Iduronic acids are the
components of glycosaminoglycans.
-L-ascorbic acid(vitamin C) is a sugar acid.
-Glucuronic acid is involved in detoxification of
bilirubin and other foreign compounds.
4-Sugar alcohols
Are formed by the reduction of the carbonyl group (aldehyde or ketone ) of
monosaccharide
5-Sugar Esters
- Hydroxyl groups of sugars can be esterified to form Acetates,
phosphates, benzoates etc.
-Sugars are phosphorylated at terminal C1 hydroxyl group or
at other places .At terminal hydroxyl: Glucose-6-P or ribose-5-P.
At C1 hydroxyl group: Glucose-1-P .At both places: Fructose 2,6
bisphosphate
- Metabolism of sugars inside the cells starts with
phosphorylation.
-Sugar phosphates are also components of nucleosides and
nucleotides.
6-Glycosides
Significance of Glycosides
1) Cardiac Glycosides- These include derivatives of digitalis
and strophanthus such as oubain.
2)Streptomycin is used as an antibiotic
3) Phloridzine -displaces Na+ from the binding site of carrier
protein and prevents the binding of sugar molecule and
produces Glycosuria.