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.
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.
Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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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