Enantioselective hydrolysis of p-nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger

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

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

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 mM 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 mM 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.

Original languageEnglish (US)
Pages (from-to)70-77
Number of pages8
JournalBiotechnology and Bioengineering
Volume49
Issue number1
DOIs
StatePublished - Jan 5 1996
Externally publishedYes

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

Keywords

  • Aspergillus niger
  • chiral synthon
  • enantiomer separation
  • epoxide hydrolase
  • optical resolution
  • p-nitrostyrene oxide

ASJC Scopus subject areas

  • Biotechnology
  • Microbiology

Cite this

Enantioselective hydrolysis of p-nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger. / Nellaiah, Hariharan; Morisseau, Christophe; Archelas, Alain; Furstoss, Roland; Baratti, Jacques C.

In: Biotechnology and Bioengineering, Vol. 49, No. 1, 05.01.1996, p. 70-77.

Research output: Contribution to journalArticle

Nellaiah, Hariharan ; Morisseau, Christophe ; Archelas, Alain ; Furstoss, Roland ; Baratti, Jacques C. / Enantioselective hydrolysis of p-nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger. In: Biotechnology and Bioengineering. 1996 ; Vol. 49, No. 1. pp. 70-77.
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