Industrial Biotransformations

Lipase
Arthrobacter sp.
1) Reaction conditions
[1]: 4.16 M, 800 g · L –1 [192.21 g · mol –1 ]
pH: 7.0
T: 40 °C
medium: two-phase: aqueous / organic
reaction type: carboxylic ester hydrolysis
catalyst: suspended enzyme
enzyme: triacylglycerol acylhydrolase (triacylglycerol lipase)
strain: Arthrobacter sp.
CAS (enzyme): [9001–62–1]
2) Remarks
O
(S,R)-1
OAc
1 = acetic acid 2-methyl-4-oxo-3-prop-2-ynyl-cyclopent-2-enyl ester
2 = 4-hydroxy-3-methyl-2-prop-2-ynyl-cyclopent-2-enone
Fig. 3.1.1.3 – 1
E
EC 3.1.1.3
OH OAc
+
O
Sumitomo Chemical Co.
● Subsequent to the lipase-catalyzed hydrolysis, the cleaved alcohol is sulfonated in the presence
of the acylated compound with methanesulfonyl chloride. The hydrolysis of the sulfonated
enantiomer in the presence of small amounts of calcium carbonate takes place under inversion
of the chiral center as opposed to the hydrolysis of the acylated enantiomer, which is carried
out under retention of the chiral center. By this means, an enantiomeric excess of 99.2 %
and a very high yield is achieved for the (R)-alcohol:
O
O
Fig. 3.1.1.3 – 2
304
(R)-1
+
OH OSO 2CH 3
O
O
(R)-2 (S)-1
CH3SO2Cl +
CaCO3
- HCl + H2O
- CH3SO3H O
(R)-3
OAc OAc
(S)-2 (S)-2
O
(S)-1
OH