The scope and limitation of the regio- and enantioselective hydrolysis of aliphatic epoxides using Bacillus subtilis epoxide hydrolase, and exploration toward chirally differentiated tris(hydroxymethyl)methanol

Ken Ichi Shimizu, Maki Sakamoto, Manabu Hamada, Toshinori Higashi, Takeshi Sugai, Mitsuru Shoji

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The substrate specificity of an engineered Bacillus subtilis epoxide hydrolase, which so far had shown high activity and enantioselectivity with 1-benzyloxymethyl-1-methyloxirane, has been studied by altering the methyl substituent into hydrogen, oxygen-containing functionalities, and unsaturated homologs. High enantioselectivity (E = 44) was observed with 1-benzyloxymethyl-1-vinyloxirane with a proper catalytic activity. The elaboration of the reaction conditions and work-up procedures enabled a preparative-scale kinetic resolution, to give (R)-2-benzyloxymethyl-3-butene-1, 2-diol and its antipodal (R)-epoxide in high ees.

Original languageEnglish
Pages (from-to)2043-2049
Number of pages7
JournalTetrahedron Asymmetry
Volume21
Issue number16
DOIs
Publication statusPublished - 2010 Aug 23

Fingerprint

Epoxide Hydrolases
Hydrolases
epoxy compounds
Bacillus
Enantioselectivity
Epoxy Compounds
Bacilli
Methanol
hydrolysis
Hydrolysis
methyl alcohol
butenes
Butenes
catalytic activity
Hydrogen
Catalyst activity
Oxygen
Kinetics
kinetics
oxygen

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

The scope and limitation of the regio- and enantioselective hydrolysis of aliphatic epoxides using Bacillus subtilis epoxide hydrolase, and exploration toward chirally differentiated tris(hydroxymethyl)methanol. / Shimizu, Ken Ichi; Sakamoto, Maki; Hamada, Manabu; Higashi, Toshinori; Sugai, Takeshi; Shoji, Mitsuru.

In: Tetrahedron Asymmetry, Vol. 21, No. 16, 23.08.2010, p. 2043-2049.

Research output: Contribution to journalArticle

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