Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide

Aya Fujino, Masayoshi Asano, Hitomi Yamaguchi, Naoki Shirasaka, Akiko Sakoda, Masaya Ikunaka, Rika Obata, Shigeru Nishiyama, Takeshi Sugai

Research output: Contribution to journal › Article

25 Citations (Scopus)

Abstract

Expeditious synthesis of (R)-bicalutamide (1), a synthetic antiandrogen, from enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether (4) was achieved. An engineered Bacillus subtilis epoxide hydrolase worked enantioselectively on the racemic epoxide (7) to provide the above starting material in highly enantiomerically enriched state.

Original languageEnglish
Pages (from-to)979-983
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number6
DOIs
Publication statusPublished - 2007 Feb 5

Fingerprint

Epoxide Hydrolases
Androgen Antagonists
Epoxy Compounds
Bacilli
Bacillus subtilis
Ether
bicalutamide

Keywords

  • (R)-1-Benzyloxy-2-methylpropane-2,3-diol
  • Bicalutamide
  • Diol
  • Epoxide hydrolase
  • Kinetic resolution

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide. / Fujino, Aya; Asano, Masayoshi; Yamaguchi, Hitomi; Shirasaka, Naoki; Sakoda, Akiko; Ikunaka, Masaya; Obata, Rika; Nishiyama, Shigeru; Sugai, Takeshi.

In: Tetrahedron Letters, Vol. 48, No. 6, 05.02.2007, p. 979-983.

Research output: Contribution to journal › Article

Fujino, A, Asano, M, Yamaguchi, H, Shirasaka, N, Sakoda, A, Ikunaka, M, Obata, R, Nishiyama, S & Sugai, T 2007, 'Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide', Tetrahedron Letters, vol. 48, no. 6, pp. 979-983. https://doi.org/10.1016/j.tetlet.2006.12.011
Fujino A, Asano M, Yamaguchi H, Shirasaka N, Sakoda A, Ikunaka M et al. Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide. Tetrahedron Letters. 2007 Feb 5;48(6):979-983. https://doi.org/10.1016/j.tetlet.2006.12.011
Fujino, Aya ; Asano, Masayoshi ; Yamaguchi, Hitomi ; Shirasaka, Naoki ; Sakoda, Akiko ; Ikunaka, Masaya ; Obata, Rika ; Nishiyama, Shigeru ; Sugai, Takeshi. / Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 6. pp. 979-983.
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