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
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
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**Instructional Text on Glycolysis Compounds**

This educational activity focuses on arranging the structures of five compounds involved in glycolysis in their proper sequential order, from the start to the end of the pathway. You are tasked with arranging these compounds without external references.

**Compounds to Arrange:**

1. **Reactant for Step 1**
2. **Product of Step 3**
3. **Product of Step 5**
4. **Product of Step 6**
5. **Product of Step 10**

**Answer Bank (Compounds):**

- Compound 1:  
  - Structure: C=O
  - CH₂-CO-CO₂²⁻

- Compound 2:
  - Structure:  
  - H-C=O
  - |  
  - C
  - |  
  - OH
  - |  
  - OH
  - |  
  - CH₂PO₃²⁻

- Compound 3:
  - Structure:  
  - CH₂OPO₃²⁻
  - |  
  - C=O
  - |  
  - HO-C-H
  - |  
  - H-C-OH
  - |  
  - H-C-OH
  - |  
  - CH₂OPO₃²⁻

- Compound 4:
  - Structure:  
  - H-C=O
  - |  
  - H-C-OH
  - |  
  - HO-C-H
  - |  
  - H-C-OH
  - |  
  - H-C-OH
  - |  
  - CH₂OH

- Compound 5:
  - Structure:  
  - A two-carbon compound with an additional phosphate group.
  
By analyzing the structural formulas provided in the answer bank, determine the correct sequence of compounds from the beginning to the end of the glycolysis process. This exercise helps reinforce knowledge about the metabolic pathway and the structural differences between intermediates.
Transcribed Image Text:**Instructional Text on Glycolysis Compounds** This educational activity focuses on arranging the structures of five compounds involved in glycolysis in their proper sequential order, from the start to the end of the pathway. You are tasked with arranging these compounds without external references. **Compounds to Arrange:** 1. **Reactant for Step 1** 2. **Product of Step 3** 3. **Product of Step 5** 4. **Product of Step 6** 5. **Product of Step 10** **Answer Bank (Compounds):** - Compound 1: - Structure: C=O - CH₂-CO-CO₂²⁻ - Compound 2: - Structure: - H-C=O - | - C - | - OH - | - OH - | - CH₂PO₃²⁻ - Compound 3: - Structure: - CH₂OPO₃²⁻ - | - C=O - | - HO-C-H - | - H-C-OH - | - H-C-OH - | - CH₂OPO₃²⁻ - Compound 4: - Structure: - H-C=O - | - H-C-OH - | - HO-C-H - | - H-C-OH - | - H-C-OH - | - CH₂OH - Compound 5: - Structure: - A two-carbon compound with an additional phosphate group. By analyzing the structural formulas provided in the answer bank, determine the correct sequence of compounds from the beginning to the end of the glycolysis process. This exercise helps reinforce knowledge about the metabolic pathway and the structural differences between intermediates.
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.

**Diagram Explanation:**

- The diagram illustrates the isomerization of glucose 6-phosphate to fructose 6-phosphate.
- On the left, the structure of glucose 6-phosphate shows the arrangement of the hydroxyl (OH) groups and a phosphate group attached to the sixth carbon.
- An arrow labeled "phosphohexose isomerase" indicates the enzymatic conversion.
- On the right, fructose 6-phosphate is depicted, showing a different arrangement of the hydroxyl groups and the same phosphate group on the sixth carbon.

**Question Section:**

Choose the statements that describe why the isomerization reaction is critical for the subsequent cleavage reaction that results in the 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 the cleavage site to stabilize the carbanion intermediate.
Transcribed Image Text: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. **Diagram Explanation:** - The diagram illustrates the isomerization of glucose 6-phosphate to fructose 6-phosphate. - On the left, the structure of glucose 6-phosphate shows the arrangement of the hydroxyl (OH) groups and a phosphate group attached to the sixth carbon. - An arrow labeled "phosphohexose isomerase" indicates the enzymatic conversion. - On the right, fructose 6-phosphate is depicted, showing a different arrangement of the hydroxyl groups and the same phosphate group on the sixth carbon. **Question Section:** Choose the statements that describe why the isomerization reaction is critical for the subsequent cleavage reaction that results in the 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 the cleavage site to stabilize the carbanion intermediate.
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