Industrial Biotransformations

Monooxygenase
Streptomyces sp. SC 1754
O
1
1) Reaction conditions
[1]: 0.015 M, 0.5 g · L –1 , [320.47 g · mol –1 ]
pH: 7.0
T: 28 °C
medium: medium B: 2 % toasted nutrisoy, 0.5 % glucose, 0.5 % yeast extract,
0.5 % K2HPO4 and 0.1 % SAG antifoam
reaction type: hydroxylation
catalyst: living whole cells
enzyme: cytochrome P-450 monooxygenase
strain: Streptomyces sp. SC 1754
2) Remarks
OH
OH
1 = mutilin
2 = (2S)-hydroxymutilin
3 = (8S)-hydroxymutilin
4 = (7S)-hydroxymutilin
Fig. 1.14.13.XX – 1
● Sariaslani and coworkers have purified and characterized the three proteins of S. griseus. Itis
likely that the same monooxygenase enzyme system is responsible for mutilin hydroxylation
by S. griseus strain SC 1754.
3) Flow scheme
Not published.
E1
HO
O
OH
OH
EC 1.14.13.XX
2 3 4
Bristol-Myers Squibb
4) Process parameters
conversion: 77.94 % (total in 7 batches)
yield: (8S)-hydroxymutilin (30.36 %), (7S)-hydroxymutilin (10.76 %),
(2S)-hydroxymutilin (7.85 %)
reactor type: batch
reactor volume: 100 L
capacity: pilot-plant
down stream processing: extraction with ethyl acetate, drying, dissolution in acetone and chloroform,
silica gel column chromatography
company: Bristol-Myers Squibb, USA
HO
O
OH
+ +
OH
O
OH
OH
OH
241