Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger

Christophe Morisseau, Hariharan Nellaiah, Alain Archelas, Roland Furstoss, Jacques C. Baratti

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

A lyophilized epoxide hydrolase preparation was isolated from the fungus Aspergillus niger. The preparation could be used in place of the whole mycelium as biocatalyst for the enantioselective hydrolysis of racemic para-nitrostyrene oxide. The cosolvent used for substrate dissolution showed slightly different effects on enzyme activity and stability. Dimethylsulfoxide (DMSO) was selected as the less inhibitory cosolvent among those tested. The enzyme preparation was first proved efficient by running a batch reactor at a low substrate concentration of 4 mM. The hydrolysis of para-nitrostyrene oxide was fast (around 5 h) and with high enantioselectivity (E = 41). The (S) enantiomer of the epoxide remained in the reaction mixture with an enantiomeric excess (ee) higher than 97% for a conversion of 47%. The substrate concentration had been optimized. It could be increased to 330 m,M (54 g l-1 without affecting the ee; therefore, the method is potentially useful for the preparative resolution of epoxides. Applications are in the field of chiral synthons which are important building blocks in organic synthesis.

Original languageEnglish (US)
Pages (from-to)446-452
Number of pages7
JournalEnzyme and Microbial Technology
Volume20
Issue number6
DOIs
StatePublished - May 1 1997
Externally publishedYes

Fingerprint

Epoxide Hydrolases
Hydrolases
Aspergillus niger
Aspergillus
Epoxy Compounds
Hydrolysis
Synthetic Chemistry Techniques
Enzyme Stability
Oxides
Mycelium
Substrates
Enzymes
Dimethyl Sulfoxide
Biocatalysts
Fungi
Enantiomers
Enantioselectivity
Batch reactors
Enzyme activity
Dissolution

Keywords

  • Aspergillus niger
  • Bioreactor
  • Enantioselectivity
  • Enzyme preparation
  • Epoxide hydrolase
  • Racemic resolution

ASJC Scopus subject areas

  • Biochemistry
  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger. / Morisseau, Christophe; Nellaiah, Hariharan; Archelas, Alain; Furstoss, Roland; Baratti, Jacques C.

In: Enzyme and Microbial Technology, Vol. 20, No. 6, 01.05.1997, p. 446-452.

Research output: Contribution to journalArticle

Morisseau, Christophe ; Nellaiah, Hariharan ; Archelas, Alain ; Furstoss, Roland ; Baratti, Jacques C. / Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger. In: Enzyme and Microbial Technology. 1997 ; Vol. 20, No. 6. pp. 446-452.
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