Industrial Biotransformations

Lipase
Pseudomonas cepacia
1 = cis-azetidinone acetate
2 = cis-azetidinone
Fig. 3.1.1.3 – 1
1) Reaction conditions
[1]: 0.049 M, 10 g · L –1 [205.21 g · mol –1 ]
pH: 7.0
T: 29 °C
medium: aqueous
reaction type: carboxylic ester hydrolysis
catalyst: immobilized enzyme
enzyme: triacylglycerol acylhydrolase (lipase, triacylglycerol lipase)
strain: Pseudomonas cepacia
CAS (enzyme): [9001–62–1]
2) Remarks
HN
● The enzyme is immobilized by adsorption onto polypropylene beads. It can be recycled several
times.
● The immobilized enzyme is reused for ten cycles without any loss in activity, productivity or
optical purity of the product.
● The rate of hydrolysis is determined to be 0.12 g · L –1 ·h –1 . It remains constant over ten cycles.
● At the end of the reaction the temperature is lowered to 5 °C and the agitation from 200 rpm to
50 rpm. The product (3R,4S)-azetidinone acetate precipitates from the reaction mixture.
● The immobilized enzyme floats on top of the reactor due to its hydrophobicity and is separated
by draining.
3) Flow scheme
Not published.
O
O
O
E
HN
1 (3R,4S)-1
O
O
O
+
HN
EC 3.1.1.3
O
OH
(3S,4R)-2
Bristol-Myers Squibb
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