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

doi:10.1016/j.tetlet.2006.12.011

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

28 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 language	English
Pages (from-to)	979-983
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2006.12.011
Publication status	Published - 2007 Feb 5

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.12.011

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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, 48(6), 979-983. https://doi.org/10.1016/j.tetlet.2006.12.011

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 › peer-review

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, 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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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.",

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AU - Fujino, Aya

AU - Asano, Masayoshi

AU - Yamaguchi, Hitomi

AU - Shirasaka, Naoki

AU - Sakoda, Akiko

AU - Ikunaka, Masaya

AU - Obata, Rika

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

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AB - 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.

KW - (R)-1-Benzyloxy-2-methylpropane-2,3-diol

KW - Bicalutamide

KW - Diol

KW - Epoxide hydrolase

KW - Kinetic resolution

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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

Abstract

Keywords

ASJC Scopus subject areas

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