Industrial Biotransformations

Naphthalene dioxygenase
Pseudomonas putida
● In the following figures the chemical routes are compared to the biotransformation route.
● The classical route to indigo needs three steps starting from aniline:
NH 2
+
Cl COOH
1 = phenylamine
2 = chloro-acetic acid
3 = phenylamino-acetic acid
4 = sodium salt of 1H-indole-3-ol
5 = indigo
Fig. 1.13.11.11 – 2
NaOH
1 2 3
air
N
H
EC 1.13.11.11
● A new catalytic route (Mitsui Chemicals, Japan) starts also from aniline but produces less inorganic
salts than the classical route:
NH 2
+
HO
OH
Ag catalyst
gas phase
O
● The biotransformation starts with glucose using the capability of the cells to produce tryptophan
as intermediate. The gene from Pseudomonas putida, which codes for the enzyme
naphthalene dioxygenase, is inserted into the common bacteria E. coli.
5
H
N
O
NHCH2COOH 2 NaNH2 N
H
2 ROOH
Mo(CO) 6
- 2 ROH
- H 2O
KOH-NaOH
1 2 3 4
1 = phenylamine
2 = ethane-1,2-diol
3 = 1H-indole
4 = indigo
Fig. 1.13.11.11 – 3
222
O
N
H
4
N
H
H
N
O
ONa