Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 23.5, Problem 17P
The enzyme that catalyzes the Cα → Cβ bond cleavage reaction that converts serine to glycine removes the substituent (R) bonded to the α-carbon in the first step of the reaction. Starting with PLP bound to serine in an imine linkage, propose a mechanism for this reaction.(Hint: The first step involves removal of the proton from serine’s OH group.)
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Students have asked these similar questions
For the following compound:
HO
-H
Draw a mechanism for the tautomerization
process under BASIC conditions:
Mechanism A:
H-O:
H-OH
H-O
HH
H-OO
Mechanism B:
H-Q
Mechanism C:
Θ
OH
H-O:
Mechanism D:
H-O
H-
H-OO
C
H-OO
H-
H-
H-OO
HH
OH
-H
-
HON H
:OH
H-H
identify the product (or multiple products) for
each of the following reactions:
CI
1) NaNH2 (excess)
ठ
Cl
2) H₂O
Hz
H₂SO₂, H₂O
HgSO
Lindlar's catalyst
1) n-BuLi
2)
1)9-BBN
2) H₂O, NaOH
?
Br
H
A
B
C
afó gó
H
OA
B
O c
OD
E
OF
D
E
F
H
H
Na, NH
Identify the product (or multiple products) for
each of the following reactions:
?
or
CI
CI 1) NaNHz (excess)
2) H₂O
OA
OB
O C
OD
OE
OF
H₂SO₂, H₂O
Hq50.
1) n-BuLi
2)
Br
1) 9-BBN
2) H₂O₂, NaOH
A
B
H H
متته
D
E
H
H
H
H
C
H
H
F
H H
H₂
Lindlar's catalyst
Na NH
Chapter 23 Solutions
Organic Chemistry (8th Edition)
Ch. 23.1 - Prob. 2PCh. 23.1 - Prob. 3PCh. 23.2 - How many conjugated double bonds are there in a....Ch. 23.2 - Instead of adding to the 4a position and...Ch. 23.2 - Prob. 7PCh. 23.3 - Prob. 8PCh. 23.3 - Acetolactate synthase is another TPP-requiring...Ch. 23.3 - Acetolactate synthase transfers the acyl group of...Ch. 23.3 - Prob. 12PCh. 23.5 - Which compound is more easily decarboxylated?
Ch. 23.5 - Prob. 14PCh. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - The enzyme that catalyzes the C C bond cleavage...Ch. 23.5 - Propose a mechanism for the ,-elimination reaction...Ch. 23.6 - Ethanolamine ammonia lyase, a coenzyme...Ch. 23.6 - Prob. 20PCh. 23.7 - How do the structure of tetrahydrofolate and...Ch. 23.7 - What is the source of the methyl group in...Ch. 23.8 - Thiols such as ethanethiol and propanethiol can be...Ch. 23 - How does the metal ion in carboxypeptidase A...Ch. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - For each of the following reactions, name both the...Ch. 23 - Prob. 27PCh. 23 - When transaminated, the three branched-chain amino...Ch. 23 - What acyl groups have we seen transferred by...Ch. 23 - Propose a mechanism for the following reaction:Ch. 23 - Draw the products of the following reaction, where...Ch. 23 - When UMP is dissolved in T2O, exchange of T for H...Ch. 23 - Dehydratase is a PLP-requiring enzyme that...Ch. 23 - In addition to the reaction mentioned in Section...Ch. 23 - PLP can catalyze both ,-elimination reactions...Ch. 23 - The glycine cleavage system is a group of four...Ch. 23 - Prob. 37PCh. 23 - FADH2 reduces , -unsaturated thioesters to...
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