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Directed evolution of an esterase for the stereoselective resolution of a key intermediate in the synthesis of epothilones

✍ Scribed by Uwe T. Bornscheuer; Josef Altenbuchner; Hartmut H. Meyer

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
123 KB
Volume
58
Category
Article
ISSN
0006-3592

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✦ Synopsis

The directed evolution of an esterase from Pseudomonas fluorescens using the mutator strain Epicurian coli XL1-Red was investigated. Mutants were as- sayed for their ability to hydrolyze a sterically hindered 3-hydroxy ester, which can serve as a building block in the synthesis of epothilones. Screening was performed by plating esterase producing colonies derived from mutation cycles onto minimal media agar plates containing indicator substances (neutral red and crystal violet). Esterase-catalyzed hydrolysis of the 3-hydroxy ester (ethyl or glycerol ester) was detected by the formation of a red color due to a pH decrease caused by the released acid. Esterases isolated from positive clones were used in preparative biotransformations of the ethyl ester. One variant containing two mutations (A209D and L181V) stereoselectively hydrolyzed the ethyl ester resulting in 25% ee for the remaining ester.

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