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CARBOHYDRATES Dr CARBOHYDRATES Dr. Phadnaik Fru Man Glu Carbohydrates Sugar alcohol Mono sacch. Oligosacch. Di sacch. (lactose) Pentoses Disacch. Plant (sucrose, maltose Sources & Trehalose) Animal Sources polysaccharides small amount (not important) Starch Carbohydrates (glycans) have the following basic composition: I (CH2O)n or H - C - OH I Monosaccharides - simple sugars with multiple OH groups. Based on number of carbons (3, 4, 5, 6), a monosaccharide is a triose, tetrose, pentose or hexose. Disaccharides - 2 monosaccharides covalently linked. Oligosaccharides - a few monosaccharides covalently linked. Polysaccharides - polymers consisting of chains of monosaccharide or disaccharide units. MONOSACCHARIDES Aldoses (e.g., glucose) have Ketoses (e.g., fructose) have an aldehyde group at one a keto group, usually at C2. end. H O C CH2OH H C OH C O HO C H HO C H H C OH H C OH H C OH H C OH CH OH CH2OH 2 D-glucose D-fructose D- D- D- Glucose Mannose Galactose CHO CHO CHO H OH H OH HO H HO H HO H HO H HO H H OH H OH H OH H OH H OH CH2OH CH OH 2 CH2OH CH2OH C O HO C H H C OH H C OH CH2OH D-fructose D VS L DESIGNATION CHO CHO D & L designations are based on the H C OH HO C H configuration about CH2OH CH2OH the single asymmetric C in D-glyceraldehyde L-glyceraldehyde glyceraldehyde. CHO CHO The lower H C OH HO C H representations are CH OH CH OH Fischer Projections. 2 2 D-glyceraldehyde L-glyceraldehyde SUGAR NOMENCLATURE O H O H For sugars with more C C than one chiral center, H – C – OH HO – C – H HO – C – H H – C – OH D or L refers to the H – C – OH HO – C – H asymmetric C farthest H – C – OH HO – C – H CH2OH CH2OH from the aldehyde or D-glucose L-glucose keto group. Most naturally occurring sugars are D isomers. D & L sugars are mirror images of one another. They have the same name, e.g., D-glucose & L-glucose. O H O H C C Other stereoisomers H – C – OH HO – C – H HO – C – H H – C – OH have unique names, H – C – OH HO – C – H e.g., glucose, mannose, H – C – OH HO – C – H CH2OH CH2OH galactose, etc. D-glucose L-glucose The number of stereoisomers is 2n, where n is the number of asymmetric centers. The 6-C aldoses have 4 asymmetric centers. Thus there are 16 stereoisomers (8 D-sugars and 8 L-sugars). HEMIACETAL & HEMIKETAL FORMATION H H An aldehyde can react with C O + R' OH R' O C OH an alcohol to R R form a aldehyde alcohol hemiacetal hemiacetal. R R A ketone can react with an C O + "R OH "R O C OH alcohol to form R' R' a hemiketal. ketone alcohol hemiketal Monosaccharides have hydroxyl and carbonyl groups in the same molecule and those with five or more carbons exist almost entirely as five- and six- membered cyclic hemiacetals. Anomeric carbon: The new stereocenter created as a result of cyclic hemiacetal formation. Anomers: Carbohydrates that differ in configuration at their anomeric carbons named a and b. CHO Pentoses and 1 H C OH hexoses can 2 cyclize as the HO C H ketone or 3 D-glucose H C OH (linear form) aldehyde reacts 4 with a distal OH. H C OH 5 Glucose forms an CH2OH intra-molecular 6 6 hemiacetal, as the 6CH2OH CH2OH 5 5 C1 aldehyde & H O H H O OH C5 OH react, to H H form a 6-member 4 OH H 1 4 OH H 1 pyranose ring, OH OH OH H 3 2 3 2 named after H OH H OH pyran. a-D-glucose b-D-glucose These representations of the cyclic sugars are called Haworth projections. 1CH2OH 2 C O HO C H 3 HOH2C 6 O 1CH2OH H C OH 4 5 H HO 2 H C OH H 5 4 3 OH OH H 6CH2OH D-fructose (linear) a-D-fructofuranose Fructose forms either a 6-member pyranose ring, by reaction of the C2 keto group with the OH on C6, or a 5-member furanose ring, by reaction of the C2 keto group with the OH on C5. 6 6CH2OH CH2OH 5 5 H O H H O OH H H 4 OH H 1 4 OH H 1 OH OH OH H 3 2 3 2 H OH H OH a-D-glucose b-D-glucose Cyclization of glucose produces a new asymmetric center at C1. The 2 stereoisomers are called anomers, a & b. Haworth projections represent the cyclic sugars as having essentially planar rings, with the OH at the anomeric C1: a (OH below the ring) b (OH above the ring). H OH H OH 4 6 H O H O HO 5 HO HO 2 H HO OH 3 H OH 1 H OH H OH H H a-D-glucopyranose b-D-glucopyranose Because of the tetrahedral nature of carbon bonds, pyranose sugars actually assume a "chair" or "boat" configuration, depending on the sugar. The representation above reflects the chair configuration of the glucopyranose ring more accurately than the Haworth projection. SUGAR DERIVATIVES COOH CHO CH OH 2 H C OH H C OH H C OH HO C H HO C H H C OH H C OH H C OH H C OH H C OH H C OH CH2OH CH2OH COOH D-ribitol D-gluconic acid D-glucuronic acid sugar alcohol - lacks an aldehyde or ketone; e.g., ribitol. sugar acid - the aldehyde at C1, or OH at C6, is oxidized to a carboxylic acid; e.g., gluconic acid, glucuronic acid. SUGAR DERIVATIVES CH2OH CH2OH H O H H O H H H OH H OH H OH OH OH O OH H NH2 H N C CH3 H a-D-glucosamine a-D-N-acetylglucosamine amino sugar - an amino group substitutes for a hydroxyl. An example is glucosamine. The amino group may be acetylated, as in N-acetylglucosamine. AMINO SUGARS Amino sugar: A sugar that contains an -NH2 group in place of an -OH group. Only three amino sugars are common in nature N-Acetyl-D-glucosamine is a derivative of D-glucosamine. CHO CHO CHO CHO O 2 H NH2 H2 N H H NH2 H NHCCH3 HO H HO H HO H HO H H OH H OH HO 4 H H OH H OH H OH H OH H OH CH2 OH CH2 OH CH2 OH CH2 OH D-Glucosamine D-Mannosamine D-Galactosamine N-Acetyl-D- glucosamine O H O COO H3C C NH R HC OH H H R = HC OH H OH CH2OH OH H N-acetylneuraminate (sialic acid) N-acetylneuraminate (N-acetylneuraminic acid, also called sialic acid) is often found as a terminal residue of oligosaccharide chains of glycoproteins. Sialic acid imparts negative charge to glycoproteins, because its carboxyl group tends to dissociate a proton at physiological pH, as shown here. Deoxy Sugars. Carbohydrates that are missing a hydroxy group. 1 1 CHO CHO 2 H 2 OH H H HOH C OH HOH2C OH 3 2 O 3 O H OH H H H OH H H 4 4 H OH H H H OH H H H OH OH 5 OH 5 CH2OH CH2OH D-ribose 2-Deoxy-D-ribose 1 1 CHO CHO 6 6 HO 2 H H HO 2 H H 3 5 3 5 O H OH H O OH H OH H OH CH OH CH3 4 4 2 4 4 H OH H HO 2 H OH H HO 2 5 H 5 H HO H HO 3 HO H HO 3 6 1 6 1 CH2OH OH H CH3 OH H L-Galactose 6-Deoxy-L-Galactose (fucose) 19 HOH2C HOH2C HO HO O O HO O OH HO C OH HN 2 HN CH H 3 H O O N-acetyl-D-glucosamine N-Acetylmuramic acid (GlcNAc or NAG) (MurNAc) REDUCTION TO ALDITOLS, ALDEHYDE ALCOHOL The carbonyl group of a monosaccharide can be reduced to an hydroxyl group by a variety of reducing agents, including NaBH4 and H2/M. CHO CH2 OH H OH H OH CH2 OH HO O HO H HO H HO NaBH4 OH H OH H OH OH H OH H OH b-D-Glucopyranose CH2 OH CH2 OH D-Glucose D-Glucitol (D-Sorbitol) An alditol OTHER ALDITOLS Other alditols common in the biological world are: CH2 OH HO H CH2 OH CH2 OH HO H H OH H OH H OH HO H H OH H OH H OH CH2 OH CH2 OH CH2 OH Erythritol D-Mannitol Xylitol EXAMPLE: ALKYLATION OF METHYL A-D- GLUCOPYRANOSIDE HOCH2 O HO + 4CH3I HO OH OCH3 Ag2O, CH3OH EXAMPLE: ALKYLATION OF METHYL A-D- GLUCOPYRANOSIDE HOCH2 O HO + 4CH3I HO OH OCH3 Ag2O, CH3OH CH3OCH2 O CH3O (97%) CH3O CH3O OCH3 Alkylation of the OH Groups OXIDATIONS Oxidation can be done in several ways. + Tollens reagent (Ag (NH3)2 or Benedict’s solution (Cu2+ tartrate complex). Not synthetically useful due to side reactions. Bromine water oxidizes aldoses (not ketoses) to monocarboxylic acids (Aldonic Acids). Nitric Acid oxidizes aldoses to dicarboxylic acids (Aldaric acids). Enzyme catalyzed oxidation of terminal OH to carboxylic acid (Uronic Acid) Periodic Acid oxidizes and breaks C C bonds. Later for that. REDUCING SUGARS Sugars with aldehyde (or ketone group) in solution. The group can be oxidized and is detected with Tollens or Benedicts solution.
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