Please draw the complete, detailed mechanism of the reaction step by step.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.60P
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Please draw the complete, detailed mechanism of the reaction step by step.

Peptides can be held in their three-dimensional shape with the help of disulfide bridges. Of the 20 amino acids
found in proteins, only cysteine contains a thiol group. In order to make a disulfide bridge, an oxidant, such as Br2,
can be used. Draw the complete, detailed mechanism of the following di-cysteine disulfide bridge formation.
-SH
H₂N
HO
+
HS-
H₂N OH
Br₂
H₂N-
HO
S
V
S-
H₂N
OH
+
HBr
Transcribed Image Text:Peptides can be held in their three-dimensional shape with the help of disulfide bridges. Of the 20 amino acids found in proteins, only cysteine contains a thiol group. In order to make a disulfide bridge, an oxidant, such as Br2, can be used. Draw the complete, detailed mechanism of the following di-cysteine disulfide bridge formation. -SH H₂N HO + HS- H₂N OH Br₂ H₂N- HO S V S- H₂N OH + HBr
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