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. OPO3²- Enz-SH 0 H-C-OH CH₂OPO3²- 3-phosphoglycerate ܘ ATP ADP O CH₂CH3 -0⁰° H-C-OH substitute for 1,3-bisphosphoglycerate CH₂OPO3²- 1,3-bisphosphoglycerate CH3 SHI substitute for Enz-SHI O=C • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. H H-C-OH glyceraldehyde 3-phosphate Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this intermediate. To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH. O CH₂OPO3²- PO4³- S-Enz H-C-OH CH₂OPO3²- (Enzyme-bound thioester) NADH/H* NAD*, Enz-SH • Do not include lone pairs in your answer. They will not be considered in the grading. • 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. OPO3²- Enz-SH 0 H-C-OH CH₂OPO3²- 3-phosphoglycerate ܘ ATP ADP O CH₂CH3 -0⁰° H-C-OH substitute for 1,3-bisphosphoglycerate CH₂OPO3²- 1,3-bisphosphoglycerate CH3 SHI substitute for Enz-SHI O=C • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. H H-C-OH glyceraldehyde 3-phosphate Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this intermediate. To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH. O CH₂OPO3²- PO4³- S-Enz H-C-OH CH₂OPO3²- (Enzyme-bound thioester) NADH/H* NAD*, Enz-SH • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw phosphate groups, when present, as in the question: in basic form and with a phosphorous oxygen double bond. .
Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Section21.SE: Something Extra
Problem 41MP
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Question
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.
-OPO3²- Enz-SH
H-C-OH
ATP
CH₂OPO3²-
3-phosphoglycerate
O
0-0--0
O
ADP
CH₂CH3
substitute for
1,3-bisphosphoglycerate
C
H-C-OH
CH₂OPO3²-
1,3-bisphosphoglycerate
O=C
CH3-SH
substitute for
Enz-SH
H
H-C-OH
|
CH₂OPO3²-
PO4³-
O.
S-Enz
H-C-OH
glyceraldehyde 3-phosphate
Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this
intermediate.
To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH.
CH₂OPO3²-
(Enzyme-bound
thioester)
NADH/H*
NAD*, Enz-SH
•
You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Draw phosphate groups, when present, as in the question: in basic form and with a phosphorous oxygen double bond.
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