F1 F2 Glycerol Glycerol-phosphate DHAP АТР ADP NAD NADH F3 Pyruvate F4 F7 F6 F5 Ethanol Acetaldehyde Acetyl-phosphate Acetate NAD NADH NAD NADH ADP АТР Ethanol is an important biofuel. In certain situations, glycerol and acetate are waste products. As the above network indicates, glycerol and acetate can be converted into ethanol. Begin by focusing on the reaction acetate + ATP +> acetyl-phosphate + ADP, AGº= 13 kJ/mol (A) Considering the reaction in isolation (e.g. acetate kinase in a test tube), given that at equilibrium [ATP] = 5 mM, [ADP] = 0.5 mM, [acetate] = 20 mM, what is equilibrium concentration of acetyl- phosphate? You may use RT = 2.5 kJ/mol. (B) Assuming the following cellular concentrations: [ATP] = 5 mM, [ADP]= 0.5 mM, [acetate] = 20 mM, and net flux in the direction shown on the diagram above, what can you say about the cellular concentration of acetyl-phosphate? (C) Draw the reactants and products of the above reaction and propose a sensible reaction mechanism using the arrow formalism (You can abbreviate the non-reacting part in ATP as R). (D) Name (or otherwise clearly indicate) one reaction in glycolysis that involves analogous functional group transformation. (E) What are 3 features that make the terminal phosphate of ATP "high energy"? (F) What is one feature that gives the phosphate bond within acetyl-phosphate high energy? Now consider the reaction pyruvate → acetaldehyde. (G) This reaction involves C-C bond breakage. What is the position of the reactive C-C bond relative to the carbonyl of pyruvate? (H) What cofactor might facilitate the reaction? (1) Propose a sensible mechanism involving the cofactor using the arrow formalism. Hint: the mechanism does not involve lipoic acid and NAD+, only the cofactor in (H).

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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F1
F2
Glycerol
• Glycerol-phosphate
DHAP
АТР
ADP
NAD
NADH
F3
Pyruvate
F4
F7
F6
F5
Ethanol
Acetaldehyde
Acetyl-phosphate •
Acetate
NAD
NADH
NAD
NADH
ADP
АТР
Ethanol is an important biofuel. In certain situations, glycerol and acetate are waste products. As the
above network indicates, glycerol and acetate can be converted into ethanol.
Begin by focusing on the reaction acetate + ATP E→ acetyl-phosphate + ADP, AG"= 13 kJ/mol
(A) Considering the reaction in isolation (e.g. acetate kinase in a test tube), given that at equilibrium
[ATP] = 5 mM, [ADP] = 0.5 mM, [acetate] = 20 mM, what is equilibrium concentration of acetyl-
phosphate? You may use RT = 2.5 kJ/mol.
(B) Assuming the following cellular concentrations: [ATP] = 5 mM, [ADP]= 0.5 mM, [acetate] = 20
mM, and net flux in the direction shown on the diagram above, what can you say about the
cellular concentration of acetyl-phosphate?
(C) Draw the reactants and products of the above reaction and propose a sensible reaction
mechanism using the arrow formalism (You can abbreviate the non-reacting part in ATP as R).
(D) Name (or otherwise clearly indicate) one reaction in glycolysis that involves analogous
functional group transformation.
(E) What are 3 features that make the terminal phosphate of ATP “high energy"?
(F) What is one feature that gives the phosphate bond within acetyl-phosphate high energy?
Now consider the reaction pyruvate → acetaldehyde.
(G) This reaction involves C-C bond breakage. What is the position of the reactive C-C bond relative
to the carbonyl of pyruvate?
(H) What cofactor might facilitate the reaction?
(1) Propose a sensible mechanism involving the cofactor using the arrow formalism. Hint: the
mechanism does not involve lipoic acid and NAD+, only the cofactor in (H).
Transcribed Image Text:F1 F2 Glycerol • Glycerol-phosphate DHAP АТР ADP NAD NADH F3 Pyruvate F4 F7 F6 F5 Ethanol Acetaldehyde Acetyl-phosphate • Acetate NAD NADH NAD NADH ADP АТР Ethanol is an important biofuel. In certain situations, glycerol and acetate are waste products. As the above network indicates, glycerol and acetate can be converted into ethanol. Begin by focusing on the reaction acetate + ATP E→ acetyl-phosphate + ADP, AG"= 13 kJ/mol (A) Considering the reaction in isolation (e.g. acetate kinase in a test tube), given that at equilibrium [ATP] = 5 mM, [ADP] = 0.5 mM, [acetate] = 20 mM, what is equilibrium concentration of acetyl- phosphate? You may use RT = 2.5 kJ/mol. (B) Assuming the following cellular concentrations: [ATP] = 5 mM, [ADP]= 0.5 mM, [acetate] = 20 mM, and net flux in the direction shown on the diagram above, what can you say about the cellular concentration of acetyl-phosphate? (C) Draw the reactants and products of the above reaction and propose a sensible reaction mechanism using the arrow formalism (You can abbreviate the non-reacting part in ATP as R). (D) Name (or otherwise clearly indicate) one reaction in glycolysis that involves analogous functional group transformation. (E) What are 3 features that make the terminal phosphate of ATP “high energy"? (F) What is one feature that gives the phosphate bond within acetyl-phosphate high energy? Now consider the reaction pyruvate → acetaldehyde. (G) This reaction involves C-C bond breakage. What is the position of the reactive C-C bond relative to the carbonyl of pyruvate? (H) What cofactor might facilitate the reaction? (1) Propose a sensible mechanism involving the cofactor using the arrow formalism. Hint: the mechanism does not involve lipoic acid and NAD+, only the cofactor in (H).
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