Flexibility of lipase brought about by solvent effects controls its enantioselectivity in organic media

Shin ichi Ueji, Tomohiko Taniguchi, Takashi Okamoto, Keiichi Watanabe, Yasuhito Ebara, Hitoshi Ohta

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The behavior of the enantioselectivity of Candida rugosa lipase was investigated in the esterification of 2-(4-substituted phenoxy)propionic acids with 1-butanol in aliphatic, aromatic, and ethereal solvents. The observed enantioselectivity (E value) was greatly affected by the solvent nature. Two key solvent characteristics, dielectric constant (e) and hydrophobicity (log P), failed to explain the solvent effects on the E value. On the other hand, the variation of the E value was found to be successfully correlated with the lipase flexibility brought about by the solvent effects, the flexibility of which was estimated by the ESR measurements of the spin-labeled lipase. Although organic chemists should often undertake a solvent screening step in the biocatalytic asymmetric resolutions, the obtained correlation will provide a useful guide in the solvent optimization step.

Original languageEnglish
Pages (from-to)399-403
Number of pages5
JournalBulletin of the Chemical Society of Japan
Volume76
Issue number2
DOIs
Publication statusPublished - 2003
Externally publishedYes

Fingerprint

Enantioselectivity
Lipase
1-Butanol
Candida
Propionates
Esterification
Hydrophobicity
Paramagnetic resonance
Screening
Permittivity

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Flexibility of lipase brought about by solvent effects controls its enantioselectivity in organic media. / Ueji, Shin ichi; Taniguchi, Tomohiko; Okamoto, Takashi; Watanabe, Keiichi; Ebara, Yasuhito; Ohta, Hitoshi.

In: Bulletin of the Chemical Society of Japan, Vol. 76, No. 2, 2003, p. 399-403.

Research output: Contribution to journalArticle

Ueji, Shin ichi ; Taniguchi, Tomohiko ; Okamoto, Takashi ; Watanabe, Keiichi ; Ebara, Yasuhito ; Ohta, Hitoshi. / Flexibility of lipase brought about by solvent effects controls its enantioselectivity in organic media. In: Bulletin of the Chemical Society of Japan. 2003 ; Vol. 76, No. 2. pp. 399-403.
@article{90ff3829c42949dfa1e33d66bc72a986,
title = "Flexibility of lipase brought about by solvent effects controls its enantioselectivity in organic media",
abstract = "The behavior of the enantioselectivity of Candida rugosa lipase was investigated in the esterification of 2-(4-substituted phenoxy)propionic acids with 1-butanol in aliphatic, aromatic, and ethereal solvents. The observed enantioselectivity (E value) was greatly affected by the solvent nature. Two key solvent characteristics, dielectric constant (e) and hydrophobicity (log P), failed to explain the solvent effects on the E value. On the other hand, the variation of the E value was found to be successfully correlated with the lipase flexibility brought about by the solvent effects, the flexibility of which was estimated by the ESR measurements of the spin-labeled lipase. Although organic chemists should often undertake a solvent screening step in the biocatalytic asymmetric resolutions, the obtained correlation will provide a useful guide in the solvent optimization step.",
author = "Ueji, {Shin ichi} and Tomohiko Taniguchi and Takashi Okamoto and Keiichi Watanabe and Yasuhito Ebara and Hitoshi Ohta",
year = "2003",
doi = "10.1246/bcsj.76.399",
language = "English",
volume = "76",
pages = "399--403",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "Chemical Society of Japan",
number = "2",

}

TY - JOUR

T1 - Flexibility of lipase brought about by solvent effects controls its enantioselectivity in organic media

AU - Ueji, Shin ichi

AU - Taniguchi, Tomohiko

AU - Okamoto, Takashi

AU - Watanabe, Keiichi

AU - Ebara, Yasuhito

AU - Ohta, Hitoshi

PY - 2003

Y1 - 2003

N2 - The behavior of the enantioselectivity of Candida rugosa lipase was investigated in the esterification of 2-(4-substituted phenoxy)propionic acids with 1-butanol in aliphatic, aromatic, and ethereal solvents. The observed enantioselectivity (E value) was greatly affected by the solvent nature. Two key solvent characteristics, dielectric constant (e) and hydrophobicity (log P), failed to explain the solvent effects on the E value. On the other hand, the variation of the E value was found to be successfully correlated with the lipase flexibility brought about by the solvent effects, the flexibility of which was estimated by the ESR measurements of the spin-labeled lipase. Although organic chemists should often undertake a solvent screening step in the biocatalytic asymmetric resolutions, the obtained correlation will provide a useful guide in the solvent optimization step.

AB - The behavior of the enantioselectivity of Candida rugosa lipase was investigated in the esterification of 2-(4-substituted phenoxy)propionic acids with 1-butanol in aliphatic, aromatic, and ethereal solvents. The observed enantioselectivity (E value) was greatly affected by the solvent nature. Two key solvent characteristics, dielectric constant (e) and hydrophobicity (log P), failed to explain the solvent effects on the E value. On the other hand, the variation of the E value was found to be successfully correlated with the lipase flexibility brought about by the solvent effects, the flexibility of which was estimated by the ESR measurements of the spin-labeled lipase. Although organic chemists should often undertake a solvent screening step in the biocatalytic asymmetric resolutions, the obtained correlation will provide a useful guide in the solvent optimization step.

UR - http://www.scopus.com/inward/record.url?scp=0037245983&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037245983&partnerID=8YFLogxK

U2 - 10.1246/bcsj.76.399

DO - 10.1246/bcsj.76.399

M3 - Article

AN - SCOPUS:0037245983

VL - 76

SP - 399

EP - 403

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 2

ER -