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Enantioselective hydrolysis of p ‐nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger
Author(s) -
Nellaiah Hariharan,
Morisseau Christophe,
Archelas Alain,
Furstoss Roland,
Baratti Jacques C.
Publication year - 2000
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/(sici)1097-0290(19960105)49:1<70::aid-bit9>3.0.co;2-q
Subject(s) - epoxide hydrolase , chemistry , aspergillus niger , epoxide , enantiomeric excess , hydrolysis , bioconversion , substrate (aquarium) , kinetic resolution , biocatalysis , organic chemistry , enantiomer , enantioselective synthesis , enzyme , chromatography , fermentation , catalysis , microsome , reaction mechanism , biochemistry , oceanography , geology
The epoxide hydrolase activity of Aspergillus niger was synthesized during growth of the fungus and was shown to be associated with the soluble cell fraction. An enzyme preparation was worked out which could be used in place of the whole mycelium as biocatalyst for the hydrolysis of epoxides. The effect of four different cosolvents on enzyme activity was investigated. Consequently, dimethylsulfoxide (DMSO) was selected for epoxide solubilization. The effect of temperature on both reaction rate and enzyme stability was studied in the presence of DMSO (0.2 volume ratio). A temperature of 25°C was selected for the reaction of bioconversion. With a substrate concentration of 4.5 m M a batch reactor showed that the enzyme preparation hydrolyzed para ‐nitrostyrene oxide with very high enantioselectivity. The (S) enantiomer of the epoxide remained in the reaction mixture and showed an enantiomeric excess higher than 99%. The substrate concentration could be increased to 20 m M without affecting the enantiomeric excess and degree of conversion. Therefore, the method is potentially useful for the preparative resolution of epoxides. Application are in the field of chiral synthons which are important building blocks in organic synthesis. © 1996 John Wiley & Sons, Inc.