Homework Help is Here – Start Your Trial Now!
Science
Biochemistry
Choose the statements that describe why the isomerization reaction is critical for the subsequent cleavage reaction that results in formation of two three-carbon sugars in the glycolytic pathway. The carbon of a carbonyl group has a partial positive charge and can delocalize electrons to facilitate cleavage of the C-C bond. Without the isomerization reaction, C-1 will be the carbonyl carbon and the C-C cleavage will occur between C-2 and C-3. Breaking a C-C bond is energetically unfavorable and can only proceed if a functional group with electronegative atoms is adjacent to the cleavage site to stabilize the reaction intermediates. To cleave a C-C bond, a nucleophilic carbon attacks the adjacent electrophilic carbon. The isomerization reaction moves the carbonyl group to C-2, thus making it a nucleophile that can attack C-3 to generate two three-carbon sugars. ☐ The partial positive charge on the carbonyl carbon can stabilize the carbon radicals formed by the homolytic cleavage of the C-C bond in the six-carbon sugar. Since the C-C cleavage occurs between C-3 and C-4 of the six-carbon sugar, the carbonyl group needs to be on C-2. Cleavage of a C-C bond in the six-carbon sugar occurs via a decarboxylation reaction that requires a carbonyl group adjacent to cleavage site to stabilize the carbanion intermediate.

Choose the statements that describe why the isomerization reaction is critical for the subsequent cleavage reaction that results in formation of two three-carbon sugars in the glycolytic pathway. The carbon of a carbonyl group has a partial positive charge and can delocalize electrons to facilitate cleavage of the C-C bond. Without the isomerization reaction, C-1 will be the carbonyl carbon and the C-C cleavage will occur between C-2 and C-3. Breaking a C-C bond is energetically unfavorable and can only proceed if a functional group with electronegative atoms is adjacent to the cleavage site to stabilize the reaction intermediates. To cleave a C-C bond, a nucleophilic carbon attacks the adjacent electrophilic carbon. The isomerization reaction moves the carbonyl group to C-2, thus making it a nucleophile that can attack C-3 to generate two three-carbon sugars. ☐ The partial positive charge on the carbonyl carbon can stabilize the carbon radicals formed by the homolytic cleavage of the C-C bond in the six-carbon sugar. Since the C-C cleavage occurs between C-3 and C-4 of the six-carbon sugar, the carbonyl group needs to be on C-2. Cleavage of a C-C bond in the six-carbon sugar occurs via a decarboxylation reaction that requires a carbonyl group adjacent to cleavage site to stabilize the carbanion intermediate.

Biochemistry
Biochemistry
6th Edition
ISBN:9781305577206
Author:Reginald H. Garrett, Charles M. Grisham
Publisher:Reginald H. Garrett, Charles M. Grisham
Chapter18: Glycolysis
Section: Chapter Questions
Problem 14P: Energetic of Fructose-1 ,6-bis P Hydrolysis (Integrates with Chapter 3.) The standard free energy...
See similar textbooks
icon
Related questions
Question
Macmillan Learning The structures of five of the compounds of glycolysis are given. Without using a reference, arrange them in order from the start of glycolysis to the end of glycolysis. Reactant for Step 1 H₂C Product of Step 3 H-C=O H-C-OH H-C- -O-PO H Product of Step 5 Answer Bank HO CH₂OPO3 CO 2- C H HTC OH H COH 2- CH₂OPO3 Product of Step 6 0=ç-0-PO, H-C OH HIC-O-PO H-C=0 H Product of Step 10 C-OH но- C-H H C-OH H-C-OH CH₂OH
Transcribed Image Text:Macmillan Learning The structures of five of the compounds of glycolysis are given. Without using a reference, arrange them in order from the start of glycolysis to the end of glycolysis. Reactant for Step 1 H₂C Product of Step 3 H-C=O H-C-OH H-C- -O-PO H Product of Step 5 Answer Bank HO CH₂OPO3 CO 2- C H HTC OH H COH 2- CH₂OPO3 Product of Step 6 0=ç-0-PO, H-C OH HIC-O-PO H-C=0 H Product of Step 10 C-OH но- C-H H C-OH H-C-OH CH₂OH
Macmillan Learning In the glycolytic pathway, glucose 6-phosphate, a six-carbon sugar, is isomerized to fructose 6-phosphate. Two steps after the isomerization reaction, the six-carbon sugar is cleaved to form two three-carbon sugars. H- -OH H H-C- -OH HO H-C-OH CH₂OPO Glucose 6-phosphate phosphohexose isomerase H H-C-OH O HO-C-H H-C-OH H-C -OH CH₂OPO Fructose 6-phosphate Choose the statements that describe why the isomerization reaction is critical for the subsequent cleavage reaction that results in formation of two three-carbon sugars in the glycolytic pathway. The carbon of a carbonyl group has a partial positive charge and can delocalize electrons to facilitate cleavage of the C-C bond. Without the isomerization reaction, C-1 will be the carbonyl carbon and the C-C cleavage will occur between C-2 and C-3. Breaking a C-C bond is energetically unfavorable and can only proceed if a functional group with electronegative atoms is adjacent to the cleavage site to stabilize the reaction intermediates. To cleave a C-C bond, a nucleophilic carbon attacks the adjacent electrophilic carbon. The isomerization reaction moves the carbonyl group to C-2, thus making it a nucleophile that can attack C-3 to generate two three-carbon sugars. The partial positive charge on the carbonyl carbon can stabilize the carbon radicals formed by the homolytic cleavage of the C-C bond in the six-carbon sugar. Since the C-C cleavage occurs between C-3 and C-4 of the six-carbon sugar, the carbonyl group needs to be on C-2. Cleavage of a C-C bond in the six-carbon sugar occurs via a decarboxylation reaction that requires a carbonyl group adjacent to cleavage site to stabilize the carbanion intermediate.
Transcribed Image Text:Macmillan Learning In the glycolytic pathway, glucose 6-phosphate, a six-carbon sugar, is isomerized to fructose 6-phosphate. Two steps after the isomerization reaction, the six-carbon sugar is cleaved to form two three-carbon sugars. H- -OH H H-C- -OH HO H-C-OH CH₂OPO Glucose 6-phosphate phosphohexose isomerase H H-C-OH O HO-C-H H-C-OH H-C -OH CH₂OPO Fructose 6-phosphate Choose the statements that describe why the isomerization reaction is critical for the subsequent cleavage reaction that results in formation of two three-carbon sugars in the glycolytic pathway. The carbon of a carbonyl group has a partial positive charge and can delocalize electrons to facilitate cleavage of the C-C bond. Without the isomerization reaction, C-1 will be the carbonyl carbon and the C-C cleavage will occur between C-2 and C-3. Breaking a C-C bond is energetically unfavorable and can only proceed if a functional group with electronegative atoms is adjacent to the cleavage site to stabilize the reaction intermediates. To cleave a C-C bond, a nucleophilic carbon attacks the adjacent electrophilic carbon. The isomerization reaction moves the carbonyl group to C-2, thus making it a nucleophile that can attack C-3 to generate two three-carbon sugars. The partial positive charge on the carbonyl carbon can stabilize the carbon radicals formed by the homolytic cleavage of the C-C bond in the six-carbon sugar. Since the C-C cleavage occurs between C-3 and C-4 of the six-carbon sugar, the carbonyl group needs to be on C-2. Cleavage of a C-C bond in the six-carbon sugar occurs via a decarboxylation reaction that requires a carbonyl group adjacent to cleavage site to stabilize the carbanion intermediate.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 4 steps with 1 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Biochemistry
Biochemistry
Biochemistry
ISBN:
9781305577206
Author:
Reginald H. Garrett, Charles M. Grisham
Publisher:
Cengage Learning
SEE MORE TEXTBOOKS