大二上 温州医学院第一临床学院-14sugars-ye.pptVIP

Two diastereomers, called anomers, are produced, with the hemiacetal carbon referred to as anomeric center. + b- (64%) a- (36%) α-D-Glucopyranose β-D-Glucopyranose D-Glucose D-glucose 3. Anomeric hydroxyl trans to the CH2OH:a anomer; cis to the CH2OH: b anomer . Haworth projection Relationship between open-chain form and Haworth projection b–D-glucopyranose a–D-glucopyranose 1. Oxygen atom at the upper right of the hexagon 2. Terminal CH2OH is up: D-sugar 4.Other group：left in Fischer’s, up in Haworth’s; right in Fischer’s, down in Haworth’s. Classroom exercise Try to write out the Haworth perspective formula from the Fischer projection formula of D-mannose. 3. Conformational formula of D-glucose b-D-(+)-Glucopyranose a-D-(+)-Glucopyranose D-glucose Open-chain form (36%) (64%) Q 2 Draw chair conformations of b-D-galactopyranose and of b-D-mannopyranose. Label the ring substituents as either axial or equatorial. Which would you expect to be more stable－galactose or mannose? D-Mannose D-Galactose b-D-Galactopyranose D-Galactose a-D-Galactopyranose b-D-mannopyranose a-D-mannopyranose D-Mannose m.p. 150℃ [α]＝+18.7° This change in optical rotation towards an equilibrium value is called mutarotation. Mutarotation +52.3 ° 4. Mutarotation 52.3o +52.3o α-anomer (+112o) β-anomer(+18.7o) Fig 15-2 Mutarotation of glucose in water solution Time 36% 64% D-ribose 5. D-Ribose D-deoxyribose D-deoxyribose a-D-ribofuranose Ⅱ. Properties of Monosaccharides Chemical Properties Oxidation : Reducing sugars Tollens’ or Benedict’s Reagents D-Gluconic acid + Ag↓ Fructose reduces Tollens’ reagent even though it contains no aldehyde group, WHY? Epimerization of Sugars in Base D-Glucose and D-mannose are C2-epimer. OH- Distereomers that differ in configuration at only one chirality center are called epimers. Epimers: Tollens’ Ag↓+ …… Functional groups which give (+) test : All monosaccharides that can directly or indirectly reduce F