chapter07

Chapter07 - BCH 4053 Summer 2001 Chapter 7 Lecture Notes Slide 1 Chapter 7 Carbohydrates Slide 2 Carbohydrates Nomenclature Hydrates of carbon

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Chapter 7, page 1 BCH 4053 Summer 2001 Chapter 7 Lecture Notes Slide 1 Chapter 7 Carbohydrates Slide 2 Carbohydrates: Nomenclature • Hydrates of carbon • General formula (CH 2 O) n (simple sugars) or C x (H 2 0) y • Monosaccharides (simple sugars) • Aldoses and ketoses • Sugar derivatives • Sugar acids, sugar alcohols, deoxy sugars, sugar esters, amino sugars, glycosides • Oligosaccharides • Polysaccharides Slide 3 Monosaccharides • Carbon chain, 1 oxygen for each carbon • One oxygen is carbonyl, rest are alcohols • Aldose—carbonyl on carbon-1 (aldehyde) • Ketose—carbonyl on carbon-2 (ketone) • Number of carbon atoms can vary • Triose, tetrose, pentose, hexose, heptose
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Chapter 7, page 2 Slide 4 Monosaccharides, stereochemistry • Chiral carbons • n-2 for aldoses (trioses have one, tetroses two, etc) • n-3 for ketoses (tetroses have one, pentoses two, etc) • Fischer projection • D correlates with d-glyceraldehyde • L correlates with l-glyceraldehyde • See Figure 7.1 Slide 5 Stereochemistry, con’t. • Number of isomers = 2 n • where n = number of chiral centers 3 8 4 16 Hexoses 2 4 3 8 Pentoses 1 2 2 4 Tetroses 0 1 1 2 Trioses Ketoses n isomers Aldoses n isomers Slide 6 Monosaccharide, nomenclature • Sugar class refers to the penultimate (n-1) carbon configuration • D sugar if n-1 position has D configuration • L sugar if n-1 position has L configuration • Isomers at other positions distinguished by different names • See Figure 7.2 for aldoses, 7.3 for ketoses
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Chapter 7, page 3 Slide 7 Monosaccharide, nomenclature, con’t. • Learn the following structures: • Trioses: all • Tetroses: all • Pentoses: ribose, ribulose, xylulose • Hexoses: glucose, mannose, galactose, fructose Slide 8 Some stereochemical terms • Enantiomers, mirror image isomers • Configuration at every chiral carbon is different • See Figure 7.4 • Diastereomers, isomers with one or more configuration differences that are not enantiomers • Epimers, isomers that differ only at one chiral center Slide 9 Acetals and Ketals • Aldehydes can react with alcohols to form hemiacetals and acetals • Ketones can react with alcohols to form hemiketals and ketals R CH O R' OH R CH OH O R O O H + hemiacetal acetal H + R C O O R R C OH O R R' OH R C O R" " " hemiketal ketal + + The aldehyde and hemiacetal are in equilibrium, and depend on the concentration of the alcohol.
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This note was uploaded on 05/22/2011 for the course BCH 4053 taught by Professor Logan during the Fall '06 term at FSU.

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Chapter07 - BCH 4053 Summer 2001 Chapter 7 Lecture Notes Slide 1 Chapter 7 Carbohydrates Slide 2 Carbohydrates Nomenclature Hydrates of carbon

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