Arrange the steps in the reaction catalyzed by threonine dehydrates in order, using the racemization reaction shown in part B as a guide. Note that the threonine dehydrates reaction is not a racemization, but instead features an elimination at the ß carbon of threonine.

Biochemistry
6th Edition
ISBN:9781305577206
Author:Reginald H. Garrett, Charles M. Grisham
Publisher:Reginald H. Garrett, Charles M. Grisham
Chapter26: Synthesis And Degradation Of Nucleotides
Section: Chapter Questions
Problem 16P
icon
Related questions
Question

Please answer this question and put them in order.

O Macmillan Learning
Threonine can be broken down by the enzyme threonine dehydratase, which catalyzes the conversion of threonine to
a-ketobutyrate and ammonia as shown in part A of the figure. The enzyme uses PLP as a cofactor. The general mechanism of
PLP-dependent racemization is shown in part B of the figure.
A
B
R- -C COO-
H
L-Amino
acid
Enz
+ NH3
Lys
+
H
‚N+
НО.
H₂C
CH
H
CH3-
11-
OH
CH-CH
-B
R
НО.
NH3
H₂C
+NH
-||
COO
COO
PLP
Threonine
dehydratase
1~
H+
HO
H₂C²
R
с
||
+NH
CH
CH₂ CH₂
COO
1/m
Quinonoid intermediate
a-Ketobutyrate
HO
R
H-C-COO-
H₂C
COO + NH, + H,O
+NH
||
CH
Lys-NH₂
Enz
R
H-C
+NH₂
3
COO-
D-Amino
acid
Pyridoxal phosphate
(internal aldimine form,
on regenerated enzyme)
Arrange the steps in the reaction catalyzed by threonine dehydrates in order, using the racemization reaction shown in part B as
a guide. Note that the threonine dehydrates reaction is not a racemization, but instead features an elimination at the ß carbon
of threonine.
Transcribed Image Text:O Macmillan Learning Threonine can be broken down by the enzyme threonine dehydratase, which catalyzes the conversion of threonine to a-ketobutyrate and ammonia as shown in part A of the figure. The enzyme uses PLP as a cofactor. The general mechanism of PLP-dependent racemization is shown in part B of the figure. A B R- -C COO- H L-Amino acid Enz + NH3 Lys + H ‚N+ НО. H₂C CH H CH3- 11- OH CH-CH -B R НО. NH3 H₂C +NH -|| COO COO PLP Threonine dehydratase 1~ H+ HO H₂C² R с || +NH CH CH₂ CH₂ COO 1/m Quinonoid intermediate a-Ketobutyrate HO R H-C-COO- H₂C COO + NH, + H,O +NH || CH Lys-NH₂ Enz R H-C +NH₂ 3 COO- D-Amino acid Pyridoxal phosphate (internal aldimine form, on regenerated enzyme) Arrange the steps in the reaction catalyzed by threonine dehydrates in order, using the racemization reaction shown in part B as a guide. Note that the threonine dehydrates reaction is not a racemization, but instead features an elimination at the ß carbon of threonine.
Macmillan Learning
Arrange the steps in the reaction catalyzed by threonine dehydrates in order, using the racemization reaction shown in part B as
a guide. Note that the threonine dehydrates reaction is not a racemization, but instead features an elimination at the ß carbon
of threonine.
First event
Final event
Answer Bank
Threonine forms an aldimine bond with PLP, displacing lysine.
Reversal of the link to PLP releases dehydrated threonine from PLP
Proton abstraction at an a carbon leads to ß elimination of —OH.
Hydrolysis of dehydrated threonine releases ammonia.
Rearrangement of an enamine forms an imine.
Transcribed Image Text:Macmillan Learning Arrange the steps in the reaction catalyzed by threonine dehydrates in order, using the racemization reaction shown in part B as a guide. Note that the threonine dehydrates reaction is not a racemization, but instead features an elimination at the ß carbon of threonine. First event Final event Answer Bank Threonine forms an aldimine bond with PLP, displacing lysine. Reversal of the link to PLP releases dehydrated threonine from PLP Proton abstraction at an a carbon leads to ß elimination of —OH. Hydrolysis of dehydrated threonine releases ammonia. Rearrangement of an enamine forms an imine.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 4 steps with 1 images

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
Biology: The Dynamic Science (MindTap Course List)
Biology: The Dynamic Science (MindTap Course List)
Biology
ISBN:
9781305389892
Author:
Peter J. Russell, Paul E. Hertz, Beverly McMillan
Publisher:
Cengage Learning
Human Heredity: Principles and Issues (MindTap Co…
Human Heredity: Principles and Issues (MindTap Co…
Biology
ISBN:
9781305251052
Author:
Michael Cummings
Publisher:
Cengage Learning