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Solutions for Amino Acids, Peptides, and Proteins
– NH3
two rapid
proton transfers
mechanism of acid hydrolysis of the nitrile
13 (b) continued
R C N C NR H N HR C C NR H
O HH
C N
O H
C N HRR H
O H
H
N
H
O H
C HR C NR H
O H
H
C NR H
HO
N
H
HOHH
C
OH H
HO
HR R C
O H
OH C OH
O H
R
R C
O H
OHH3N CH
CH2Ph
COOH
14
(a)
NH3, HCN
(b)
(c)
NH3, HCN
∆
∆
H2N CH
CH2CH(CH3)2
CNC H
CH2CH(CH3)2
O
H2N CH
CH2COO
CNC H
CH2COOH
O
CH COOH
CH2COOH
H3N
CH COOH
CH2CH(CH3)2
H3N
H2OH+
H2O
H+
H2O
H2O
H+
H2O
H2O
H2O
H3O+
H3O+
NH3, HCN
∆H2N CH
CH(CH3)2
CNC H
CH(CH3)2
O
CH COOH
CH(CH3)2
H3NH2O
H3O+
before acidification
634