c. The biosynthesis of valine by bacteria involves the following sequence: O (CH3)2CHCCO₂H (CH3)2C-CHCO₂H OH OH (CH3)2CHCHCO₂H 1 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-d3 of the 2R, 3R configuration produces 2S,3S-valine-d3, whereas the 2R, 3S diol-d3 produces 2S,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.

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Chapter1: Chemical Foundations
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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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