Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate.

Chemistry
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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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  • You do not have to consider stereochemistry.
  • You do not have to explicitly draw H atoms.
  • Do not include lone pairs in your answer.
  • Draw phosphate groups, when present, as in the question: in basic form and with a phosphorous oxygen double bond.
One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol
group on the enzyme to give an enzyme-bound thioester, and reduction with NADH.
O
-OPO3²-
H-C-OH
ATP ADP
CH₂OPO3²-
3-phosphoglycerate
80-8-0
CH₂CH3
H-C-OH
Enz-SH
CH₂OPO3²-
1,3-bisphosphoglycerate
-S-CH3 substitute for the
enzyme-bound
thioester
O=C
-H
H-C-OH
I
CH₂OPO3²-
PO4³-
3-
O=C
S-Enz
H-C-OH
I
CH₂OPO3²-
(Enzyme-bound
thioester)
NADH/H+
NAD*, Enz-SH
glyceraldehyde 3-phosphate
Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate.
To simplify the drawing process, substitute the structure below for the enzyme-bound thioester.
27
Transcribed Image Text:One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. O -OPO3²- H-C-OH ATP ADP CH₂OPO3²- 3-phosphoglycerate 80-8-0 CH₂CH3 H-C-OH Enz-SH CH₂OPO3²- 1,3-bisphosphoglycerate -S-CH3 substitute for the enzyme-bound thioester O=C -H H-C-OH I CH₂OPO3²- PO4³- 3- O=C S-Enz H-C-OH I CH₂OPO3²- (Enzyme-bound thioester) NADH/H+ NAD*, Enz-SH glyceraldehyde 3-phosphate Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate. To simplify the drawing process, substitute the structure below for the enzyme-bound thioester. 27
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