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
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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Question
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.
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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