Industrial Biotransformations

d-Aminoacid oxidase
Trijonopsis variabilis
HOOC
1) Reaction conditions
[1]: 0.02 M, 7.47 g · L –1 [373.38 g · mol –1 ]
pH: 7.3
T: 25 °C
medium: aqueous
reaction type: oxidative deamination
catalyst: immobilized enzyme
enzyme: d-amino-acid oxygen oxidoreductase, deaminating (d-amino-acid oxidase)
strain: Trijonopsis variabilis
CAS (enzyme): [9000–88–8]
2) Remarks
● This step is part of the 7-aminocephalosporanic acid (7-ACA) process, see page 326.
EC 1.4.3.3
● Ketoadipinyl-7-ACA decarboxylates in situ in presence of H 2O 2 that is formed by the biotransformation
step yielding glutaryl-7-ACA:
HOOC
NH 2
O
O
1 = α-ketoadipinyl-7-ACA
2 = glutaryl-7-ACA
Fig. 1.4.3.3 – 2
1 2
1 = Cephalosporin C
2 = N-α-ketoadipinyl-7-aminocephalosporanic acid Sandoz AG
Fig. 1.4.3.3 – 1
O
H
N
O
H
N
O
N
S
COOH
N
S
COOH
O
O
O
O
E
+H2O
+O2 - NH3
- H2O2 H 2O 2
- CO2
HOOC
HOOC
1 2
O
O
O
H
N
O
H
N
O
N
N
S
S
COOH
COOH
O
O
O
O
209