Industrial Biotransformations

Oxidase
Rhodococcus erythropolis
2
O
1) Reaction conditions
[1]: 0.076 M, 10 g · L –1 [132.16 g · mol –1 ]
pH: 6.8 – 7.2
T: 30 °C
medium: aqueous
reaction type: oxidation
catalyst: whole cells
enzyme: hydroxylase
strain: Rhodococcus erythropolis
2) Remarks
O
(R/S)-1
OH
E
(R)-1
● The resolution is carried out by selective microbial oxidation of the (S)-enantiomer.
EC 1.X.X.X
● The chemical synthesis of (R)-isopropylideneglycerol starting from unnatural l-mannitol is difficult
and expensive:
O
O
OH
+
O
O
(R)-2
COOH
1 = isopropylideneglycerol
2 = isopropylideneglyceric acid International BioSynthetics, Inc.
Fig. 1.X.X.X – 1
HO
HO
HO
1
OH
OH
OH
1 = mannitol
2 = isopropylideneglyceric aldehyde
3 = isopropylideneglycerol
Fig. 1.X.X.X – 2
Me 2CO
ZnCl2
HO
O
O
O
O
OH
Pb(OAc)4
2
O
O
(R)-2
CHO
NaBH4
2
O
O
(R)-3
OH
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