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.. carbohydrates and glycolysis • Glycolysis: a mechanism you should know/ Aldolase 3. Hydroxyl beta to the Sc denrotonated EL

.. carbohydrates and glycolysis • Glycolysis: a mechanism you should know/ Aldolase 3. Hydroxyl beta to the Sc denrotonated EL

Biochemistry
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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Complete this mechanism
### Glycolysis: A Mechanism You Should Know / Aldolase **Step 1:** Fructose-1,6-bisphosphate binds to the enzyme. The enzyme has a lysine residue with an amino group (\(NH_2\)), which will participate in the reaction. **Step 2:** The amino group reacts with the carbonyl group of fructose-1,6-bisphosphate to form a protonated Schiff base. **Step 3:** The hydroxyl group beta to the Schiff base is deprotonated. Electrons flow into the protonated Schiff base, cleaving the aldol in the process. The first product, glyceraldehyde-3-phosphate (\(GAP\)), exits the active site. **Step 4:** The electron flow reverses out of the Schiff base and into the enamine intermediate. The carbon atom is reprotonated, stabilizing the intermediate. **Step 5:** The Schiff base is hydrolyzed, regenerating the carbonyl and releasing the second product, dihydroxyacetone phosphate (\(DHAP\)). ### Diagrams and Explanations: - **Steps 1 & 2:** Illustrations depict fructose-1,6-bisphosphate binding and forming a Schiff base with the enzyme’s lysine residue. - **Step 3:** Shows electron movement leading to the cleavage of the fructose molecule and the formation of the first product, glyceraldehyde-3-phosphate. - **Step 4:** Demonstrates the reversal of electron flow into the enamine intermediate. - **Step 5:** Illustrates the hydrolysis of the Schiff base and the release of dihydroxyacetone phosphate. Each step is depicted with chemical structures and electron flow arrows for clarity.
Transcribed Image Text:### Glycolysis: A Mechanism You Should Know / Aldolase **Step 1:** Fructose-1,6-bisphosphate binds to the enzyme. The enzyme has a lysine residue with an amino group (\(NH_2\)), which will participate in the reaction. **Step 2:** The amino group reacts with the carbonyl group of fructose-1,6-bisphosphate to form a protonated Schiff base. **Step 3:** The hydroxyl group beta to the Schiff base is deprotonated. Electrons flow into the protonated Schiff base, cleaving the aldol in the process. The first product, glyceraldehyde-3-phosphate (\(GAP\)), exits the active site. **Step 4:** The electron flow reverses out of the Schiff base and into the enamine intermediate. The carbon atom is reprotonated, stabilizing the intermediate. **Step 5:** The Schiff base is hydrolyzed, regenerating the carbonyl and releasing the second product, dihydroxyacetone phosphate (\(DHAP\)). ### Diagrams and Explanations: - **Steps 1 & 2:** Illustrations depict fructose-1,6-bisphosphate binding and forming a Schiff base with the enzyme’s lysine residue. - **Step 3:** Shows electron movement leading to the cleavage of the fructose molecule and the formation of the first product, glyceraldehyde-3-phosphate. - **Step 4:** Demonstrates the reversal of electron flow into the enamine intermediate. - **Step 5:** Illustrates the hydrolysis of the Schiff base and the release of dihydroxyacetone phosphate. Each step is depicted with chemical structures and electron flow arrows for clarity.
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