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2.14. The following questions illustrate how stereochemical considerations can be used to elucidate aspects of biological mechanisms and reactions. a. A mixture of ³H-labeled 14-A and 14-B was carried through the reaction sequence shown: CO₂ H3+N-H H 14-A T -OH H HO 14-B CO₂ -N+H3 H

2.14. The following questions illustrate how stereochemical considerations can be used to elucidate aspects of biological mechanisms and reactions. a. A mixture of ³H-labeled 14-A and 14-B was carried through the reaction sequence shown: CO₂ H3+N-H H 14-A T -OH H HO 14-B CO₂ -N+H3 H

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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2.14. The following questions illustrate how stereochemical considerations can be used to elucidate aspects of biological mechanisms and reactions. a. A mixture of ³H-labeled 14-A and 14-B was carried through the reaction sequence shown: CO2- H3*N- H+N*H3 H OH НО — Н 14-A 14-B D-aminoacid glycolate HOCH,CHCO, oxidase HOCH,CCO,H H2O2 oxidase HOCH,CO2H HCCO,H N*H3 D-amino acid oxidase will oxidize only serine having R configuration at C(2). Glycolate oxidase will remove only the pro-R hydrogen of glycolic acid. Does the product (O=CHCO,H) contain tritium? Explain your reasoning. b. Enzymatic oxidation of naphthalene by bacteria proceeds by way of the inter- mediate cis-diol shown. Which prochiral face of C(1) and C(2) of naphthalene is hydroxylated in this process? OH OH
Transcribed Image Text:2.14. The following questions illustrate how stereochemical considerations can be used to elucidate aspects of biological mechanisms and reactions. a. A mixture of ³H-labeled 14-A and 14-B was carried through the reaction sequence shown: CO2- H3*N- H+N*H3 H OH НО — Н 14-A 14-B D-aminoacid glycolate HOCH,CHCO, oxidase HOCH,CCO,H H2O2 oxidase HOCH,CO2H HCCO,H N*H3 D-amino acid oxidase will oxidize only serine having R configuration at C(2). Glycolate oxidase will remove only the pro-R hydrogen of glycolic acid. Does the product (O=CHCO,H) contain tritium? Explain your reasoning. b. Enzymatic oxidation of naphthalene by bacteria proceeds by way of the inter- mediate cis-diol shown. Which prochiral face of C(1) and C(2) of naphthalene is hydroxylated in this process? OH OH
c. The biosynthesis of valine by bacteria involves the following sequence: (CH3)2C-CHCO2H (CH3)2CHCCO,H (CH3)2CHCHCO,H ОН ОН NH2 The stereochemistry of the reaction has been examined using the starting diol in which each methyl group was separately replaced by CD3. The diol-d, the 2R,3R configuration produces 2S,3S-valine-d, whereas the 2R,35 diol-d, produces 25,3R-valine-d3. From this information deduce whether the C(2) and C(3) hydroxy are replaced with inversion or retention of configuration. Show the basis for your conclusion. d. A synthesis of the important biosynthetic intermediate mevalonic acid starts with the enzymatic hydrolysis of the diester 14-C by pig liver esterase. The pro-R ester group is selectively hydrolyzed. Draw a three-dimensional structure of the product. of CH3 H3CO2CCH,CCH,CO2CH3 1. ОН 14-C
Transcribed Image Text:c. The biosynthesis of valine by bacteria involves the following sequence: (CH3)2C-CHCO2H (CH3)2CHCCO,H (CH3)2CHCHCO,H ОН ОН NH2 The stereochemistry of the reaction has been examined using the starting diol in which each methyl group was separately replaced by CD3. The diol-d, the 2R,3R configuration produces 2S,3S-valine-d, whereas the 2R,35 diol-d, produces 25,3R-valine-d3. From this information deduce whether the C(2) and C(3) hydroxy are replaced with inversion or retention of configuration. Show the basis for your conclusion. d. A synthesis of the important biosynthetic intermediate mevalonic acid starts with the enzymatic hydrolysis of the diester 14-C by pig liver esterase. The pro-R ester group is selectively hydrolyzed. Draw a three-dimensional structure of the product. of CH3 H3CO2CCH,CCH,CO2CH3 1. ОН 14-C
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