S.11.215E3KEYV2 - Name_ Page 1 S.11.215E3 I. (27 points) A....

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Name_____________________________ I. (27 points) Page 1 S.11.215E3 C OH H H HO H HO OH H CH 2 OH C HO H HO H H OH HO H CH 2 OH C H HO H HO OH H OH H CH 2 OH C H HO H HO H HO OH H CH 2 OH D-galactose L-gulose D-mannose D-talose 2. When treated with NaBH 4 , which aldohexose provides a product that is chiral but has only 3 peaks in the 13 C NMR spectrum? Circle one. 3. Dilute HNO 3 converts both the aldehyde and the primary alcohol of an aldohexose into carboxylic acid groups to provide a product called an aldaric acid. Which of the above aldohexoses provides an achiral (meso) aldaric acid upon treatment with dilute HNO 3 ? 4. Treatment of D-glucose with aqueous base can result in an aldohexose that is the C2-epimer of D-glucose. Which aldohexose would be formed? O OH H H HO H H OH H OH OH 5. Lactose or milk sugar is a disaccharide derived from the aldopyranose below and ! -D-glucose. Which aldohexose does the aldopyranose shown below correspond to? O OH H CH 2 OH HO H H OH H H OH 6. Which aldohexose above corresponds to the aldopyranose depicted below? A. Consider the aldohexoses below: O H O H O H O H D-galactose L-gulose D-mannose D-talose R or S R or S R or S R or S 1. Circle the correct stereochemical configuration for each stereocenter: 3 3 3 3 3 3 3 3 3 D-galactose L-gulose D-mannose D-talose D-galactose L-gulose D-mannose D-talose D-galactose L-gulose D-mannose D-talose D-galactose L-gulose D-mannose D-talose
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Name_____________________________ II. (34 points) Page 2 S.11.215E3 HO N H H N OH O NH 3 O O O pK a values = 2.1 (CO 2 H) 3.5 (CO 2 H) 8.7 (R 1 side chain) 9.6 (NH 3 + ) When glutathione is treated with excess CH 3 OH and HCl, a product with two methyl esters is formed. The side chain of the central residue readily undergoes Michael reactions with ! , " - unsaturated ketones. contains the most acidic proton in glutathione isoelectric point = 5.0 L-amino acid with a single stereocenter in an R configuration isoelectric point = 6.1 optically inactive A. Provide the full name of the N-terminal amino acid residue in glutathione.
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This note was uploaded on 09/21/2011 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.

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S.11.215E3KEYV2 - Name_ Page 1 S.11.215E3 I. (27 points) A....

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