Industrial Biotransformations

Lipase
Pseudomonas fluorescens
Fig. 3.1.1.3 – 1
1) Reaction conditions
pH: 7.0
T: 25 °C
medium: aqueous
reaction type: carboxylic ester hydrolysis
catalyst: solubilized enzyme
enzyme: triacylglycerol acylhydrolase (lipase, triacylglycerol lipase)
strain: Pseudomonas fluorescens
CAS (enzyme): [9001–62–1]
2) Remarks
● The hydrolysis is preferred over the transesterification in this case since the reaction rate and
enantioselectivity of the acylation are drastically reduced.
● Continuous addition of NaOH to the reaction mixture during hydrolysis is necessary to maintain
neutral pH.
● If a hydrophobic ester (e.g. butyrate) is used, the ester can be extracted into the organic phase
(heptane), while the alcohol remains in the aqueous phase.
● The butyrate ester is insoluble in water, so that after centrifugation and separation of the aqueous
phase the alcohol can be easily extracted and purified by crystallization.
● About ten percent of the ester are lost because of pH-dependent ring-opening to an unstable
carboxylic acid salt.
3) Flow scheme
Not published.
EC 3.1.1.3
Celltech Group plc
291