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Carbohydrates-1

Classification Metabolism

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Carbohydrates
Most abundant in nature Functions: • Energy storage (starch, glycogen) • Metabolic precursors • Structural (cellulose, glycoproteins, glycolipids) • Communication (lectinsglycoproteins, glycolipids) • Industrial applications

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where n > 3 Monosaccharides Disaccharides Oligosaccharides Polysaccharides 3 .Carbohydrates • • • • • • Saccharides (sugar) (CH2O)n.

Monosaccharides 4 .

ketopentose 5 .Nomenclature Linear form and carbon numbering Nature of carbonyl group Aldehyde (aldose) or Ketone (ketose) Number of carbon atoms 3C (triose). pentulose Combinations Aldohexose. 6C (hexose) Insert ‘ul’ for ketose Tetrulose.

Optical activity right (+) and left (-) rotation 6 .

D.Stereochemistry Fischer projection Horizontal bonds – above page Vertical bonds – below page • if the OH group on the highest numbered asymmetric carbon is to the right in Fischer projection L. • if OH is on the left 7 .

C2 and Clast excluded 2n-3 stereoisomer Epimers (differ in one center) Enantiomers (mirror images) Diastereomer (differ in more than one chiral centers but not mirror images) 8 .Stereoisomer Stereoisomer (depends on number of chiral centers) For aldose: Minimum 3 carbons C1 and Clast excluded 2n-2 stereoisomer For ketose: Minimum 4 carbons C1.

not all are useful or synthesized. 9 . But.Stereoisomers Several stereoisomers are possible for a given monosaccharide.

A 5-member sugar is called furanose (after furan) and 6member sugar is called pyranose (after pyran). 10 .Cyclic Structures Sugars with four or more carbons exist primarily in cyclic forms.

The other anomer is known as β form. In the α anomer.Cyclic Structures During cyclization. OH group at the anomeric carbon is on the opposite side of the sugar ring from the CH2OH group that designates the D or L configuration of the molecule. the carbonyl carbon (called anomeric carbon) becomes a new chiral center and the two possible diastereomers are called anomers. 11 .

Cyclic Structures A linear structure is converted to a cyclic structure. 12 .

Cyclic Structures The configurations of the substituents to each carbon in the sugar ring is presented by Haworth projection Cells do not process L-sugars The 6-membered ring exists in boat or chair conformation The CH2OH will be at the opposite side for an L-sugar 13 .

Axial and equatorial positioning of OH and H is important 14 .

Some D-aldoses (3-6 carbons) 15 .

Some D-ketoses (3-6 carbons) 16 .

the C-O bond is called glycosidic bond. (eg. formation of methyl glucoside. Glycosidic bond: When the anomeric carbon bonds to an oxygen.Some important reactions Mutarotation: Interconversion of α and β forms Saccharides bearing anomeric carbons that have not formed glycosides is called a ‘reducing sugar’. when α-D-glucose reacts with methanol) 17 .

Tetrose (4C) .Summary of Terms Property Length Cacrbonyl No. ketose Triose (3C). of C Based on Mono. di. oligo. poly Aldose. Tetrulose. β 18 .. aligned with glyceraldehyde OH position at anomeric carbon Anomeric carbon free + D Symbol Optical activity Stereomer or L Anomers Reducing α. pentulose … Rotation of polarized light (dextro or levo rotation) Asymmetry in the chiral centers Last chiral center configuration..

Disaccharides 19 .

Some disaccharides 20 .

Some Properties 2 monosaccharides Glycosidic bond α or β linked Reducing or non-reducing Homodisaccharides Heterodisaccharides Name: eg. Sucrose α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside 21 .