Industrial Biotransformations

Hydantoinase / Carbamoylase
Pseudomonas sp.
HO
HN
O
1) Reaction conditions
[1]: >0.21 M, 40 g · L –1 [192.17 g · mol –1 ]
pH: 8.0
T: 38 °C
medium: aqueous
reaction type: carboxylic acid amide hydrolysis
catalyst: whole cells
enzyme: l-5-carboxymethylhydantoin
hydrolase
amidohydrolase / N-carbamoyl-d-amino acid
strain: Pseudomonas sp.
CAS (enzyme): [9025–14–3] / –
2) Remarks
NH
O
● The strain contains both enzymes (hydantoinase and carbamoylase).
● The cell biomass is used directly in the process. Alternatively the enzymes may be extracted
and immobilized.
● Instead of hydroxyphenylglycine the non-hydroxylated phenylglycine can be produced in the
same way.
● Kanegafuchi also uses the hydantoinase to hydrolyze d,l-5-(p-hydroxyphenyl)hydantoin (see
page 411). The second step, the hydrolysis of the d-N-carbamoyl-d-hydroxyphenyl glycine is
performed either chemically with HNO 2 or enzymatically with carbamoylase.
3) Flow scheme
Not published.
HO
HN
L-1 D-1 D-2
1 = p-hydroxyphenylhydantoin
2 = N-carbamoyl amino acid
3 = α−(-) phenyl glycine
Fig. 3.5.2.4 / 3.5.1.77 – 1
O
NH
O
E
HN
O
NH2
COOH
E
+H2O + H2O
- CO(NH2)2
HO
EC 3.5.2.4 / 3.5.1.77
HO
H2N
D-3
COOH
Dr. Vig Medicaments
415