Chapter7 student - Carbohydrates Molecules for Structure...

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Unformatted text preview: Carbohydrates Molecules for Structure and Energy Storage 1 MCDB310 Chapter 7: Carbohydrates Monosaccharides one sugar unit aldehydes or ketones with two or more hydroxyl groups carbons onto which these are attached are chiral centers D-glucose (dextrose) most common names end in ose Oligosaccharides short chains of sugars joined with glycosidic bonds disaccharides are most abundant sucrose is common = D-glucose + D-fructose names end in ose Carbohydrate Classes 2 MCDB310 Chapter 7: Carbohydrates Polysaccharides usually >20 monosaccharides linked together (up to 1000s) sugar chains can be linear or branched starch and cellulose: glucose polymers that differ greatly in structure and function Carbohydrate Classes 3 MCDB310 Chapter 7: Carbohydrates backbones are unbranched carbon chains with single bonds usually contain multiple chiral carbon atoms can be open-chain or cyclic open forms have a carbonyl group aldehyde aldose ketone ketose monosaccharide names: Type of carbonyl group and number of carbon atoms Monosaccharides 4 MCDB310 Chapter 7: Carbohydrates aldehyde = aldose 3 C atoms = triose aldotriose Examples of Monosaccharides 5 MCDB310 Chapter 7: Carbohydrates chiral carbon atoms: Rotate the plane of polarized light glyceraldehyde has 1 chiral center 2 enantiomers (D and L) 2 n stereoisomers for a molecule with n chiral centers Stereochemistry of Monosaccharides D L D/L Configuration: based on the chiral center most distant from the carbonyl carbon those with the same configuration as D-glyceraldehyde are D-isomers 6 MCDB310 Chapter 7: Carbohydrates carbons are numbered beginning at the carbonyl carbon end epimers : Isomers that differ only in configuration of a single carbon (e.g. D-glucose and D-mannose, D-glucose and D-galactose) Epimers 7 MCDB310 Chapter 7: Carbohydrates all monosaccharides with >5 carbons are cyclic in aqueous soln carbonyl carbon forms hemiacetal/hemiketal with internal hydroxyl group Cyclic Isoforms of Monosaccharides 8 MCDB310 Chapter 7: Carbohydrates D-glucose forms an intramolecular hemiacetal between hydroxyl at C- 5 and aldehyde at C-1 results in 2 anomers (isomers): -D-glucopyranose and -D-glucopyranose 6-membered ring: Pyranose Mutarotation of Glucose 9 MCDB310 Chapter 7: Carbohydrates aldohexoses and aldopentoses form 6-membered ring: Pyranoses ketohexoses form 5-membered ring: Furanoses Pyranoses and Furanoses 10 MCDB310 Chapter 7: Carbohydrates...
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Chapter7 student - Carbohydrates Molecules for Structure...

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