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

研究成果: Article査読

6 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)2043-2049
ページ数7
ジャーナルTetrahedron Asymmetry
21
16
DOI
出版ステータスPublished - 2010 8月 23

ASJC Scopus subject areas

  • 触媒
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

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