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

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

27 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

Access to Document

10.1016/j.tetlet.2006.12.011

Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

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.

@article{bde73e8cbac349dfa833355455b03c3f,

title = "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 = "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.",

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

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

year = "2007",

month = feb,

day = "5",

doi = "10.1016/j.tetlet.2006.12.011",

language = "English",

volume = "48",

pages = "979--983",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "6",

}

TY - JOUR

T1 - 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

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

PY - 2007/2/5

Y1 - 2007/2/5

N2 - 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.

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

UR - http://www.scopus.com/inward/record.url?scp=33846173011&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33846173011&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.12.011

DO - 10.1016/j.tetlet.2006.12.011

M3 - Article

AN - SCOPUS:33846173011

VL - 48

SP - 979

EP - 983

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 6

ER -

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

Access to Document

Other files and links

Cite this