The transformation for the metabolism of D-glucose- 6 -phosphate to D-fructose- 6 -phosphate is to be shown as two enzyme-catalyzed keto-enol tautomerizations. Concept Introduction: A monosaccharide in which aldehyde carbonyl group is present at C1 is called aldose whereas a monosaccharide in which ketone carbonyl group is present at C2 is called ketose.

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rivatives: Nucleophilic Acyl Substitution Reactions - EOC O C-O [References] 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. H-C-OH ATP ADP CH₂OPO32- 3-phosphoglycerate 0= OPO32- C H-C-OH CH₂OPO32 1,3-bisphosphoglycerate Enz-SH PO43- O= C S-Enz H-C-OH CH₂OPO3² (Enzyme-bound thioester) NADH/H+ O=C NAD*, Enz-SH H H-C-OH CH₂OPO3²- 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. S-CH3 substitute for the CH2CH3 enzyme-bound thioester You do not have to consider stereochemistry. • You do not have…

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Chapter 20, Problem 20.81P

Interpretation Introduction

Interpretation:

The transformation for the metabolism of D-glucose- 6 -phosphate to D-fructose- 6 -phosphate is to be shown as two enzyme-catalyzed keto-enol tautomerizations.

Concept Introduction:

A monosaccharide in which aldehyde carbonyl group is present at C1 is called aldose whereas a monosaccharide in which ketone carbonyl group is present at C2 is called ketose.

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rivatives: Nucleophilic Acyl Substitution Reactions - EOC O C-O [References] 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. H-C-OH ATP ADP CH₂OPO32- 3-phosphoglycerate 0= OPO32- C H-C-OH CH₂OPO32 1,3-bisphosphoglycerate Enz-SH PO43- O= C S-Enz H-C-OH CH₂OPO3² (Enzyme-bound thioester) NADH/H+ O=C NAD*, Enz-SH H H-C-OH CH₂OPO3²- 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. S-CH3 substitute for the CH2CH3 enzyme-bound thioester You do not have to consider stereochemistry. • You do not have…

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*,…

A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. Is the product capable of showing optical activity? If it is, explain how.