Regio- and enantioselective hydrolysis of phenyloxiranes catalyzed by soluble epoxide hydrolase

Kristin C. Williamson, Christophe Morisseau, Joseph E. Maxwell, Bruce D. Hammock

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The regio- and enantioselective hydrolysis of several phenyloxiranes catalyzed by soluble epoxide hydrolase (sEH) was investigated using recombinant human, mouse or cress sEH. Results indicate that human and mouse sEH enantioselectively hydrolyze (S,S)-alkyl-phenyloxiranes faster than the (R,R)-alkyl-phenyloxiranes investigated in this study, while cress sEH displayed opposite enantioselectivity. Preparation of pure (2R,3R)-3-phenylglycidol from the racemic mixture was achieved with a 31% yield using human sEH as catalyst. The sEH enzymes were found to be regioselective at the benzylic carbon of the phenyloxiranes, supporting the proposed mechanism in which one or more tyrosine residues in the active site of the enzyme act as a general acid catalyst in the alkylation half reaction.

Original languageEnglish (US)
Pages (from-to)4451-4462
Number of pages12
JournalTetrahedron Asymmetry
Volume11
Issue number22
DOIs
StatePublished - Nov 17 2000

Fingerprint

styrene oxide
Epoxide Hydrolases
Hydrolases
epoxy compounds
hydrolysis
Hydrolysis
Brassicaceae
mice
enzymes
Enzymes
catalysts
Catalysts
Enantioselectivity
tyrosine
alkylation
Alkylation
Tyrosine
Catalytic Domain
Carbon

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Regio- and enantioselective hydrolysis of phenyloxiranes catalyzed by soluble epoxide hydrolase. / Williamson, Kristin C.; Morisseau, Christophe; Maxwell, Joseph E.; Hammock, Bruce D.

In: Tetrahedron Asymmetry, Vol. 11, No. 22, 17.11.2000, p. 4451-4462.

Research output: Contribution to journalArticle

Williamson, Kristin C. ; Morisseau, Christophe ; Maxwell, Joseph E. ; Hammock, Bruce D. / Regio- and enantioselective hydrolysis of phenyloxiranes catalyzed by soluble epoxide hydrolase. In: Tetrahedron Asymmetry. 2000 ; Vol. 11, No. 22. pp. 4451-4462.
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