Chapter-8 Saccharide Chemistry

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1 Chapter-8 Saccharide Chemistry Page

2 Carbohydrates (Saccharides) are most abundant biological molecule, riginally produced through C 2 fixation during photosynthesis I (C 2 ) n or - C - I where n 3 Monosaccharides Basic unit. Based on number of carbons (3, 4, 5, 6), a monosaccharide is a triose, tetrose, pentose or hexose. Disaccharides - 2 monosaccharides covalently linked. ligosaccharides - a few monosaccharides covalently linked. Polysaccharides - polymers consisting of chains of monosaccharide or disaccharide units.

3 Roles of Carbohydrates Energy storage (glycogen, starch) Structural components (cellulose, chitin) Cellular recognition Carbohydrate derivatives include DNA, RNA, glycoproteins, glycolipids

4 Monosaccharides are aldoses or ketoses Monosacchardes are aldehyde or ketone derivatives of straight chain polyhydroxy alcohols containing at least three carbon atoms

5 Monosaccharides Aldoses (e.g., glucose) have an aldehyde group at one end. Ketoses (e.g., fructose) have a keto group, usually at C2. C C 2 C C C C C C C C C 2 D-glucose C 2 D-fructose

6 Smallest monosaccharides are with three carbon atoms called trioses With 4 carbon atoms-----tetroses With 5 carbon atoms pentoses With 6 carbon atoms hexoses With 7 carbon atoms------heptoses

7 Aldotriose, Ketotriose, etc According to the number of carbon and functional group mono saccharde are named Aldotriose, Ketotriose, etc

8

9 Glucose is aldohexose. All except two of its six C atoms, C1 and C6 are chiral centers. So D-glucose has 24 = 16 stereoisomers When at C5 is on right, it is D sugar and its mirror image is L sugar. D sugars are more biologically abundant

10 Most common aldoses include six carbon sugar glucose, mannose and galactose C C C C C C 2 D-glucose

11 The pentose is ribose (component of ribonucleotide residue of RNA), and triose is glyceraldehyde (occurs in metabolic pathways)

12 EPIMERS Monosaccharides which differ in configuration around one specific C-atom are called epimers of one another C-2 epimers D-glucose and D-mannose

13 CARBN-2 EPIMERS C C C C C C 2 D-GLUCSE C C C C C C 2 D-MANNSE

14 Most common ketoses have ketone function at C2,have one less asymmetric center. Ketohexose has 23 = 8 possible stereoisomers

15

16 emiacetal & hemiketal formation Alcohol react with the carbonyl group of aldehydes to form a hemiacetal. Alcohol react with the carbonyl group of ketones to form a hemiketal. C R R C R' + R' R' C aldehyde alcohol hemiacetal + R R "R "R C ketone alcohol hemiketal R'

17 A sugar with six membered ring is known as pyranose. Similarly sugar with five membered ring is known as furanose

18 Monosaccharides can cyclize to form Pyranose / Furanose forms

19 aworth Projections C 1 C up = beta - down = alpha C 3 5 C C 5 C 2 When a monosaccharide cyclizes, the carbonyl carbon, called the anomeric carbon, becomes a chiral center with two possible configuration. 3 2 Anomeric carbon (most oxidized)

20 Glucose forms an intra-molecular hemiacetal, as the C1 aldehyde & C5 react, to form a 6-member pyranose ring, called glucopyranose C C C C C C C 2 D-glucose (linear form) 6 5 C D-glucose 3 2 -D-glucose These representations of the cyclic sugars are called aworth projections.

21 1 C 2 2 C C C C C 2 D-fructose (linear) 2 C C 2 Fructose forms 5-member furanose ring, by reaction of the C2 keto group with the on C5 called fructofuranose D-fructofuranose 1 2

22 4 6 5 C D-glucose C 2 -D-glucose Pair of stereoisomers that differ in configuration at anomeric carbon are called anomers, &. ( of anomeric carbon is opposite side of C2) ( of anomeric carbon is on same side of C2). Two anomers have slightly different physical and chemical properties

23 The anomers freely interconvert in aqueous solution, so at equilibrium D-glucose is a mixture of anomer (63.6%) and the anomer (36.4%). α-d-glucopyranose D-Glucose (linear form) β-d-glucopyrnose

24 Sugars Can Be Modified and Covalently Linked

25 xidation of aldose converts its aldehyde group to carboxylic acid yield aldonic acid such as gluconic acid

26 xidation of primary alcohol group of aldoses yields uronic acids.

27 Aldoses and ketoses can be reduced by treatment with NaB4 to yield polyhydroxy alcohols known as alditols

28 Ribitol is a component of flavin coenzymes, and glycerol and the cyclic polyhydroxy alcohol myoinositol are important lipid components. Xylitol is a sweetener that is used in sugarless gum and candies:

29 Monosaccharide unit in which an group is replaced by are known as deoxy sugars. Like β-d-2-deoxyribose sugar component of DNA C 2 C 2 (no ) ribose deoxyribose

30 Amino Sugars amino sugar one or more groups have been replaced by an amino group. An example is D- glucosamine and D-galactosamine.

31 Glycosidic Bonds Link the Anomeric Carbon to other Compounds

32 Glycosidic Bonds The anomeric group of a sugar can condense with an alcohol to form α and β glycosides. The bond connecting the anomeric carbon to the alcohol oxygen is termed a glycosidic bond: R- + -R' R--R' + 2 E.g., methanol reacts with the anomeric on glucose to form methyl glucoside (methyl-glucopyranose). + C 3-2 -D-glucopyranose methanol C 3 methyl- -D-glucopyranose

33 N-Glycosidic Bond It forms between the anomeric carbon and an amine, are the bond that link ribose to purine and pyrimidines in nucleic acids.

34 Reducing and Non-Reducing Sugars Saccharides (sugars) bearing anomeric carbon that have not formed glycosides are termed as reducing sugars Identification of sugar as non-reducing means that it is a glycoside.

35 Polysaccharides--Glycans Consist of monosaccharides linked together by glycosidic bonds omopolysaccharides----consist one type of monosaccharides eteropolysaccharides---consist more than one type of monosaccharides Exoglycosidases and Endoglycosidases are enzymes that hydrolyze monosaccharide units

36 Polysaccharides, in contrast to proteins and nucleic acids, form branched as well As linear polymers

37 Disaccharides Sucrose and Lactose

38 Lactose, occurs naturally in milk, conc. ranges from 0-7% depending on the species, is composed of galactose & glucose, with (1 4) indicates that glycosidic bond links C1 of β anomer of galactose to 4 of glucose. Its full name is -D-galactopyranosyl-(1 4)-Dglucopyranose Free anomeric carbon on glucose, therefore reducing sugar

39 Sucrose, common table sugar, major form in which carbohydrates are transported in plants. has a glycosidic bond linking the anomeric hydroxyls of each sugar (C1 in glucose & C2 in fructose). Because the configuration at the anomeric C of glucose is ( points down from ring), the linkage is (1 2). The full name of sucrose is -D-glucopyranosyl-(1 2)- - D-fructofuranoside Anomeric carbon of each sugar participate, hence non-reducing sugar

40 Noncarbohydrate molecules that has the taste of sucrose are used as sweeting agents In food and beverages

41 Polysaccharides Cellulose and Chitin Are Structural Polysaccharides

42 Cellulose Plants cell walls can withstand osmotic pressure difference between extra and intracellular up to 20 atm. Cellulose, a major constituent of plant cell walls, consists of long linear chains of glucose with (1 4) glycosidic linkages, contain up to 15,000 D-glucose residues

43 Cellulose chains are flat, in which successive glucose rings are turned over 180 with respect to each other, result in -bond between C3- of each glucose with ring oxygen (5) of next glucose. ther interchain - bonds are 2-6

44 Stacks of these sheets are held together by hydrogen bonds and van der Waals interactions

45 Due to that cellulose fibers becomes exceptional strength and make them water insoluble. In Plant cell wall, cellulose fibers are embedded with other polysaccharides and lignin. The resulting material can withstand large stress

46 Cellulase Glycosidase enzymes are used to hydrolyze glycosidic bond. Vertebrates do not possess enzyme capable to hydrolyze β(1 4) linkages of cellulose. Digestive tracts of herbivores contain symbiotic microorganisms that secrete cellulases. Same is true for termit Degradation of cellulose is slow process, thus cow and other ruminants must chew their cud

47 Chitin Principal structural component of exoskeleton of invertebrates like insects, spiders and also present in cell wall of fungi and algae It is homopolymer of β(1 4) linked N- acetyl D-glucsoamine residues.

48 Starch and Glycogen are storage Polysaccharides

49 Starch Plants synthesize starch as energy reserve and it is deposited in chloroplasts of cell Starch is composed of α-amylose and amylopectin

50 α-amylose is a linear polymer of several thousand glucose residues linked by (1 4) bonds. The end of the polysaccharide with an anomeric C1 not involved in a glycosidic bond is called the reducing end C 2 6C 2 C amylose C 2 C 2

51 α-amylose s α glycosidic bonds cause it to adopt an irregular aggregating coiled conformation

52 Amylopectin is a glucose polymer with mainly (1 4) linkages, but it also has branches formed by (1 6) linkages after every 24 to 30 glucose residues. Amylopectin is one of largest molecule in nature The storage of starch greatly reduces the intracellular osmotic pressure that would result from its storage in monomeric form. Starch is a reducing sugar C 2 C 2 1 amylopectin C 2 C 2 6C C 2 C 2 1 4

53 Digestion of Starch Saliva contains amylase, which randomly hydrolyzes (1 4) linkages and this digestion continues in small intestine by pancreatic amylase produce mixture of oligosaccharides. α-glucosidase further hydrolyse and remove one glucose at a time. Debranching enzymes hydrolyze (1 4) and (1 6) linkages and produce monosacchrides that are absorbed by the intestine and transported to the bloodstream.

54 Glycogen Glycogen, the glucose storage polymer in animals, is similar in structure to amylopectin. But glycogen has more (1 6) branches. With branch point after every 8 to 14 glucose residues. It is present in all cells but is most prevalent in skeletal muscle and in liver.. C 2 C 2 C 2 C 2 6C C 2 C glycogen

55 Glycogen Phosphorylase Glycogen is degraded for metabolic use by glycogen phosphorylase, which cleaves glycogen s (1 4) bond. Glycogen s highly branched structure permits rapid mobilization of glucose in times of metabolic need. (1 6) branches of glycogen are cleaved by glycogen debranching enzyme.

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