1. Opine dehydrogenases (ODH) have evolved in invertebrate marine organisms with wide-ranging physiological roles. The first class of this family of enzymes provides an alternative pathway for the lactate dehydrogenase pathway in anaerobic energy production. The lactate dehydrogenase pathway is found in higher organisms and in mammals including humans. One class of opine dehydrogenases catalyzes the reductive coupling of pyruvate to N-a-carboxyalkyl-L-amino acids represented by the re- action below: HO NH₂ + ༠༤ OH ODH HO S སྨིཾནྟཱ པཱ པ ཙཏྟཱ པཱ ཨཡཾ པཱཐ ཊྛཊྛིནཏྟི ཨཱ NAD(P)H NAD(P)* R₁ R OH R₂ where R1 is the side chain of the amino acid, R2 represents the alkyl group of the a-keto acid that is coupled to the amino acid, and NAD(P)H/NAD(P)* are the reduced/oxidized forms of nicotinamide ad- enine dinucleotide phosphate, a cofactor of the enzyme that catalyzes oxidation-reduction reactions. (a): The product of the reaction has two chiral centers as shown: The Ca atom of the amino acid containing the R₁ side chain has an S or L configuration while the Ca atom containing the R2 side chain has an R or D configuration. Using any of the representations of a tetrahedral carbon illustrated below, draw the configurations of the substituents attached to the tetrahedral carbon atoms if both the R1 and R2 side chains are methyl groups. Name the amino acid.
1. Opine dehydrogenases (ODH) have evolved in invertebrate marine organisms with wide-ranging physiological roles. The first class of this family of enzymes provides an alternative pathway for the lactate dehydrogenase pathway in anaerobic energy production. The lactate dehydrogenase pathway is found in higher organisms and in mammals including humans. One class of opine dehydrogenases catalyzes the reductive coupling of pyruvate to N-a-carboxyalkyl-L-amino acids represented by the re- action below: HO NH₂ + ༠༤ OH ODH HO S སྨིཾནྟཱ པཱ པ ཙཏྟཱ པཱ ཨཡཾ པཱཐ ཊྛཊྛིནཏྟི ཨཱ NAD(P)H NAD(P)* R₁ R OH R₂ where R1 is the side chain of the amino acid, R2 represents the alkyl group of the a-keto acid that is coupled to the amino acid, and NAD(P)H/NAD(P)* are the reduced/oxidized forms of nicotinamide ad- enine dinucleotide phosphate, a cofactor of the enzyme that catalyzes oxidation-reduction reactions. (a): The product of the reaction has two chiral centers as shown: The Ca atom of the amino acid containing the R₁ side chain has an S or L configuration while the Ca atom containing the R2 side chain has an R or D configuration. Using any of the representations of a tetrahedral carbon illustrated below, draw the configurations of the substituents attached to the tetrahedral carbon atoms if both the R1 and R2 side chains are methyl groups. Name the amino acid.
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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Transcribed Image Text:1. Opine dehydrogenases (ODH) have evolved in invertebrate marine organisms with wide-ranging
physiological roles. The first class of this family of enzymes provides an alternative pathway for the
lactate dehydrogenase pathway in anaerobic energy production. The lactate dehydrogenase pathway
is found in higher organisms and in mammals including humans. One class of opine dehydrogenases
catalyzes the reductive coupling of pyruvate to N-a-carboxyalkyl-L-amino acids represented by the re-
action below:
NH₂
ི་
ODH
HO
R
요
OH
སྨིཾནྟཱ ར པ དརཱ ཨཱཋཏྭཱ… … ཨཱསྨིཾ ཏྟཏྟིནྡནྟི ཨཱ
HO
NAD(P)H NAD(P)*
S
R₁ R₂
where R1 is the side chain of the amino acid, R2 represents the alkyl group of the a-keto acid that is
coupled to the amino acid, and NAD(P)H/NAD(P)* are the reduced/oxidized forms of nicotinamide ad-
enine dinucleotide phosphate, a cofactor of the enzyme that catalyzes oxidation-reduction reactions.
(a).
The product of the reaction has two chiral centers as shown: The Ca atom of the amino
acid containing the R₁ side chain has an S or L configuration while the Ca atom containing the R2 side
chain has an R or D configuration. Using any of the representations of a tetrahedral carbon illustrated
below, draw the configurations of the substituents attached to the tetrahedral carbon atoms if both the
R1 and R2 side chains are methyl groups. Name the amino acid.
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