Hofmeister series of ionic liquids: Kosmotropic effect of ionic liquids on the enzymatic hydrolysis of enantiomeric phenylalanine methyl ester

Hua Zhao; Sophia M. Campbell; Lee Jackson; Zhiyan Song; Olarongbe Olubajo

doi:10.1016/j.tetasy.2006.01.015

Hofmeister series of ionic liquids: Kosmotropic effect of ionic liquids on the enzymatic hydrolysis of enantiomeric phenylalanine methyl ester

Hua Zhao
, Sophia M. Campbell
, Lee Jackson
, Zhiyan Song
, Olarongbe Olubajo

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

124 Scopus citations

Abstract

The kinetic hydrolysis of enantiomeric phenylalanine methyl ester catalyzed by Bacillus licheniformis protease was performed in aqueous solutions of several hydrophilic ionic liquids (ILs). The protease enantioselectivity was found related to the kosmotropicity of individual cations and anions of ILs. The ion effectiveness in enhancing the enzyme enantioselectivity follows the Hofmeister series: kosmotropic anions and chaotropic cations stabilize the enzyme. In this application, the Hofmeister series of ILs was established in an order of decreasing effectiveness for anions: PO₄^3- > citrate^3-, CH₃COO^-, EtSO₄ ^-, CF₃COO^- > Br^- > OTs ^-, BF₄^- and for cations: [EMIM]⁺ > [BMIM]⁺ > [HMIM]⁺. The overall IL kosmotropicity was quantified by the δ value (difference in the Jones-Dole viscosity B-coefficients of anion and cation). In general, a high enzyme enantioselectivity was observed in a solution of IL with a high δ value.

Original language	English (US)
Pages (from-to)	377-383
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	17
Issue number	3
DOIs	https://doi.org/10.1016/j.tetasy.2006.01.015
State	Published - Feb 6 2006
Externally published	Yes

Bibliographical note

Funding Information:
This project was partially supported by the NIH EARDA Grant (No. 5 G11 HD 32861-08). The authors are very thankful to the anonymous reviewer for suggesting constructive improvements of the manuscript.

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10.1016/j.tetasy.2006.01.015

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title = "Hofmeister series of ionic liquids: Kosmotropic effect of ionic liquids on the enzymatic hydrolysis of enantiomeric phenylalanine methyl ester",

abstract = "The kinetic hydrolysis of enantiomeric phenylalanine methyl ester catalyzed by Bacillus licheniformis protease was performed in aqueous solutions of several hydrophilic ionic liquids (ILs). The protease enantioselectivity was found related to the kosmotropicity of individual cations and anions of ILs. The ion effectiveness in enhancing the enzyme enantioselectivity follows the Hofmeister series: kosmotropic anions and chaotropic cations stabilize the enzyme. In this application, the Hofmeister series of ILs was established in an order of decreasing effectiveness for anions: PO43- > citrate3-, CH3COO-, EtSO4 -, CF3COO- > Br- > OTs -, BF4- and for cations: [EMIM]+ > [BMIM]+ > [HMIM]+. The overall IL kosmotropicity was quantified by the δ value (difference in the Jones-Dole viscosity B-coefficients of anion and cation). In general, a high enzyme enantioselectivity was observed in a solution of IL with a high δ value.",

author = "Hua Zhao and Campbell, \{Sophia M.\} and Lee Jackson and Zhiyan Song and Olarongbe Olubajo",

note = "Funding Information: This project was partially supported by the NIH EARDA Grant (No. 5 G11 HD 32861-08). The authors are very thankful to the anonymous reviewer for suggesting constructive improvements of the manuscript.",

year = "2006",

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doi = "10.1016/j.tetasy.2006.01.015",

language = "English (US)",

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T2 - Kosmotropic effect of ionic liquids on the enzymatic hydrolysis of enantiomeric phenylalanine methyl ester

AU - Zhao, Hua

AU - Campbell, Sophia M.

AU - Jackson, Lee

AU - Song, Zhiyan

AU - Olubajo, Olarongbe

N1 - Funding Information: This project was partially supported by the NIH EARDA Grant (No. 5 G11 HD 32861-08). The authors are very thankful to the anonymous reviewer for suggesting constructive improvements of the manuscript.

PY - 2006/2/6

Y1 - 2006/2/6

N2 - The kinetic hydrolysis of enantiomeric phenylalanine methyl ester catalyzed by Bacillus licheniformis protease was performed in aqueous solutions of several hydrophilic ionic liquids (ILs). The protease enantioselectivity was found related to the kosmotropicity of individual cations and anions of ILs. The ion effectiveness in enhancing the enzyme enantioselectivity follows the Hofmeister series: kosmotropic anions and chaotropic cations stabilize the enzyme. In this application, the Hofmeister series of ILs was established in an order of decreasing effectiveness for anions: PO43- > citrate3-, CH3COO-, EtSO4 -, CF3COO- > Br- > OTs -, BF4- and for cations: [EMIM]+ > [BMIM]+ > [HMIM]+. The overall IL kosmotropicity was quantified by the δ value (difference in the Jones-Dole viscosity B-coefficients of anion and cation). In general, a high enzyme enantioselectivity was observed in a solution of IL with a high δ value.

AB - The kinetic hydrolysis of enantiomeric phenylalanine methyl ester catalyzed by Bacillus licheniformis protease was performed in aqueous solutions of several hydrophilic ionic liquids (ILs). The protease enantioselectivity was found related to the kosmotropicity of individual cations and anions of ILs. The ion effectiveness in enhancing the enzyme enantioselectivity follows the Hofmeister series: kosmotropic anions and chaotropic cations stabilize the enzyme. In this application, the Hofmeister series of ILs was established in an order of decreasing effectiveness for anions: PO43- > citrate3-, CH3COO-, EtSO4 -, CF3COO- > Br- > OTs -, BF4- and for cations: [EMIM]+ > [BMIM]+ > [HMIM]+. The overall IL kosmotropicity was quantified by the δ value (difference in the Jones-Dole viscosity B-coefficients of anion and cation). In general, a high enzyme enantioselectivity was observed in a solution of IL with a high δ value.

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U2 - 10.1016/j.tetasy.2006.01.015

DO - 10.1016/j.tetasy.2006.01.015

M3 - Article

AN - SCOPUS:33644679574

SN - 0957-4166

VL - 17

SP - 377

EP - 383

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 3

ER -

Hofmeister series of ionic liquids: Kosmotropic effect of ionic liquids on the enzymatic hydrolysis of enantiomeric phenylalanine methyl ester

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