Chapter7 student - Carbohydrates Molecules for Structure...

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Carbohydrates Carbohydrates   Molecules for Structure and Energy Storage 1 MCDB310 – Chapter 7: Carbohydrates
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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
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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
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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
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aldehyde = aldose 3 C atoms = triose aldotriose Examples of Monosaccharides 5 MCDB310 – Chapter 7: Carbohydrates
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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
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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
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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
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D-glucose forms an  intramolecular hemiacetal  between   hydroxyl at C-5 and aldehyde at C-1 results in 2  anomers  (isomers): α -D-glucopyranose and β -D-glucopyranose  6-membered ring:  Pyranose Mutarotation of Glucose 9 MCDB310 – Chapter 7: Carbohydrates
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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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