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

doi:10.1016/j.tetasy.2010.07.014

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

School of Pharmaceutical Sciences

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

6 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 language	English
Pages (from-to)	2043-2049
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	16
DOIs	https://doi.org/10.1016/j.tetasy.2010.07.014
Publication status	Published - 2010 Aug 23

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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Shimizu, K. I., Sakamoto, M., Hamada, M., Higashi, T., Sugai, T., & Shoji, M. (2010). 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. Tetrahedron Asymmetry, 21(16), 2043-2049. https://doi.org/10.1016/j.tetasy.2010.07.014

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

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

Shimizu, KI, Sakamoto, M, Hamada, M, Higashi, T, Sugai, T & Shoji, M 2010, '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', Tetrahedron Asymmetry, vol. 21, no. 16, pp. 2043-2049. https://doi.org/10.1016/j.tetasy.2010.07.014

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title = "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",

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.",

author = "Shimizu, {Ken Ichi} and Maki Sakamoto and Manabu Hamada and Toshinori Higashi and Takeshi Sugai and Mitsuru Shoji",

note = "Funding Information: The authors thank Drs. Masaya Ikunaka, Hitomi Yamaguchi and Mr. Naoki Shirasaka of the Research & Development Center, Nagase & Co., for their support on Bacillus subtilis epoxide hydrolase. This work was partly supported by the {\textquoteleft}High-Tech Research Center{\textquoteright} Project for Private Universities: matching fund subsidy 2006–2011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan , and acknowledged with thanks.",

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doi = "10.1016/j.tetasy.2010.07.014",

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AU - Sakamoto, Maki

AU - Hamada, Manabu

AU - Higashi, Toshinori

AU - Sugai, Takeshi

AU - Shoji, Mitsuru

N1 - Funding Information: The authors thank Drs. Masaya Ikunaka, Hitomi Yamaguchi and Mr. Naoki Shirasaka of the Research & Development Center, Nagase & Co., for their support on Bacillus subtilis epoxide hydrolase. This work was partly supported by the ‘High-Tech Research Center’ Project for Private Universities: matching fund subsidy 2006–2011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan , and acknowledged with thanks.

PY - 2010/8/23

Y1 - 2010/8/23

N2 - 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.

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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

Abstract

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