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The diagram below shows an outline of the aminotransferase mechanism that skips the specific steps that show how electrons flow when a Schiff base is formed or is hydrolyzed. Using the mechanistic details given below A. Draw the mechanism for Enzyme- PLP Schiff base formation using pyridoxal and the lysine amine group using arrow to indicate electron flow. B.Draw the mechanism for hydrolysis of the Schiff base to form the a-keto acid, which is the reverse of the first reaction.

The diagram below shows an outline of the aminotransferase mechanism that skips the specific steps that show how electrons flow when a Schiff base is formed or is hydrolyzed. Using the mechanistic details given below A. Draw the mechanism for Enzyme- PLP Schiff base formation using pyridoxal and the lysine amine group using arrow to indicate electron flow. B.Draw the mechanism for hydrolysis of the Schiff base to form the a-keto acid, which is the reverse of the first reaction.

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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The diagram below shows an outline of the aminotransferase mechanism that skips the specific steps that show how electrons flow when a Schiff base is formed or is hydrolyzed. Using the mechanistic details given below A. Draw the mechanism for Enzyme- PLP Schiff base formation using pyridoxal and the lysine amine group using arrow to indicate electron flow. B.Draw the mechanism for hydrolysis of the Schiff base to form the a-keto acid, which is the reverse of the first reaction.
Stage 1 Lys residue 0,PO- HO +0,PO- step / Enz #tep 2 step 3 N Enzyme-PLP Schiff base R Pyridoxine (vitamin B.) Enzyme-PLP Schiff base OH CHIE -m Amino acid H (rate determining)=0 + E¬NH₂- E "NH₂ OH 0,90 Amino acid H -Coo R-C-COO "NH₂ [H *0,90- H осного NH₂ Lys residue *0,PO- Pyridoxal phosphate (PLP) E-N-E H R > R-CO-H E Amino acid-PLP Schiff base (aldimine) (CH₂ NH₂ OH Amino acid-PLP Schiff base (aldimine) Stage 2 =Z-m 0,90- N%₂ *0,90- + H₂O NH₂ 0,PO- Exped Pyridoxamine phosphate Ketimine Schiff base a-Keto acid Ketimine Figure 17.16 Biochemistry, First Edition, Copyright © 2017 W. W. Norton & Co., Inc. Other reagents can add as well. One group of compounds that adds is amines, substituted ammonia molecules with the general formula RNH₂. The reaction mechanism is very similar to those shown for the addition of H₂O or alcohols. It is acid catalyzed. The first step of the mechanism generates a carbocation. This reacts with the lone pair of electrons on the nitrogen in the amine. The unstable product of this step is stabilized by the loss of an equivalent of water from the molecule, to form a Schiff base as shown below. a-Keto acid C-coo A. show how this forms Stage 1 Lys residue Enz Enzyme-PLP Schiff base B. show how the a-keto acid forms NH₂ 0,PO- Chala NH₂ O,PO- Ketimine a-keto acid -coo Pyridoxamine phosphate
Transcribed Image Text:Stage 1 Lys residue 0,PO- HO +0,PO- step / Enz #tep 2 step 3 N Enzyme-PLP Schiff base R Pyridoxine (vitamin B.) Enzyme-PLP Schiff base OH CHIE -m Amino acid H (rate determining)=0 + E¬NH₂- E "NH₂ OH 0,90 Amino acid H -Coo R-C-COO "NH₂ [H *0,90- H осного NH₂ Lys residue *0,PO- Pyridoxal phosphate (PLP) E-N-E H R > R-CO-H E Amino acid-PLP Schiff base (aldimine) (CH₂ NH₂ OH Amino acid-PLP Schiff base (aldimine) Stage 2 =Z-m 0,90- N%₂ *0,90- + H₂O NH₂ 0,PO- Exped Pyridoxamine phosphate Ketimine Schiff base a-Keto acid Ketimine Figure 17.16 Biochemistry, First Edition, Copyright © 2017 W. W. Norton & Co., Inc. Other reagents can add as well. One group of compounds that adds is amines, substituted ammonia molecules with the general formula RNH₂. The reaction mechanism is very similar to those shown for the addition of H₂O or alcohols. It is acid catalyzed. The first step of the mechanism generates a carbocation. This reacts with the lone pair of electrons on the nitrogen in the amine. The unstable product of this step is stabilized by the loss of an equivalent of water from the molecule, to form a Schiff base as shown below. a-Keto acid C-coo A. show how this forms Stage 1 Lys residue Enz Enzyme-PLP Schiff base B. show how the a-keto acid forms NH₂ 0,PO- Chala NH₂ O,PO- Ketimine a-keto acid -coo Pyridoxamine phosphate
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