SER-HIS-ASP catalytic triad in model non-aqueous solvent environment: A computational study

Justin Kai Chi Lau; Yuen Kit Cheng

doi:10.1016/j.bmcl.2006.08.083

SER-HIS-ASP catalytic triad in model non-aqueous solvent environment: A computational study

Justin Kai Chi Lau, Yuen Kit Cheng^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

2 Citations (Scopus)

Abstract

Emerging new properties and applications of enzymes in organic solvents and ionic liquids are unabating. By applying a combined Quantum Mechanics/Continuum Mechanics computation on a prototypical catalytic triad serine-histidine-aspartate (SER-HIS-ASP) interacting with ethanol or acetonitrile molecules, the major difference between protic and aprotic solvents in effecting transition-state stabilization has been analyzed. Moderately polar aprotic solvent acetonitrile is predicted to be unable to stabilize the transition state in replacing the role of the oxyanion-hole environment, whereas protic ethanol solvent molecules of similar polarity to acetonitrile are adequate in re-gaining the enzymatic activities.

Original language	English
Pages (from-to)	5797-5800
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2006.08.083
Publication status	Published - 15 Nov 2006

Scopus Subject Areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

User-Defined Keywords

Catalytic triad
Non-aqueous solvent
QM/CM

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10.1016/j.bmcl.2006.08.083

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title = "SER-HIS-ASP catalytic triad in model non-aqueous solvent environment: A computational study",

abstract = "Emerging new properties and applications of enzymes in organic solvents and ionic liquids are unabating. By applying a combined Quantum Mechanics/Continuum Mechanics computation on a prototypical catalytic triad serine-histidine-aspartate (SER-HIS-ASP) interacting with ethanol or acetonitrile molecules, the major difference between protic and aprotic solvents in effecting transition-state stabilization has been analyzed. Moderately polar aprotic solvent acetonitrile is predicted to be unable to stabilize the transition state in replacing the role of the oxyanion-hole environment, whereas protic ethanol solvent molecules of similar polarity to acetonitrile are adequate in re-gaining the enzymatic activities.",

keywords = "Catalytic triad, Non-aqueous solvent, QM/CM",

author = "Lau, {Justin Kai Chi} and Cheng, {Yuen Kit}",

note = "Funding Information: We cordially thank Mr. Morris Law for the computational support and would like to acknowledge the financial support from the Hong Kong Research Grant Committee (HKBU 2029/00P) and HKBU FRG/99-00/II-34-P making this work possible. ",

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doi = "10.1016/j.bmcl.2006.08.083",

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AU - Lau, Justin Kai Chi

AU - Cheng, Yuen Kit

N1 - Funding Information: We cordially thank Mr. Morris Law for the computational support and would like to acknowledge the financial support from the Hong Kong Research Grant Committee (HKBU 2029/00P) and HKBU FRG/99-00/II-34-P making this work possible.

PY - 2006/11/15

Y1 - 2006/11/15

N2 - Emerging new properties and applications of enzymes in organic solvents and ionic liquids are unabating. By applying a combined Quantum Mechanics/Continuum Mechanics computation on a prototypical catalytic triad serine-histidine-aspartate (SER-HIS-ASP) interacting with ethanol or acetonitrile molecules, the major difference between protic and aprotic solvents in effecting transition-state stabilization has been analyzed. Moderately polar aprotic solvent acetonitrile is predicted to be unable to stabilize the transition state in replacing the role of the oxyanion-hole environment, whereas protic ethanol solvent molecules of similar polarity to acetonitrile are adequate in re-gaining the enzymatic activities.

AB - Emerging new properties and applications of enzymes in organic solvents and ionic liquids are unabating. By applying a combined Quantum Mechanics/Continuum Mechanics computation on a prototypical catalytic triad serine-histidine-aspartate (SER-HIS-ASP) interacting with ethanol or acetonitrile molecules, the major difference between protic and aprotic solvents in effecting transition-state stabilization has been analyzed. Moderately polar aprotic solvent acetonitrile is predicted to be unable to stabilize the transition state in replacing the role of the oxyanion-hole environment, whereas protic ethanol solvent molecules of similar polarity to acetonitrile are adequate in re-gaining the enzymatic activities.

KW - Catalytic triad

KW - Non-aqueous solvent

KW - QM/CM

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U2 - 10.1016/j.bmcl.2006.08.083

DO - 10.1016/j.bmcl.2006.08.083

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SN - 0960-894X

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JF - Bioorganic and Medicinal Chemistry Letters

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ER -

SER-HIS-ASP catalytic triad in model non-aqueous solvent environment: A computational study

Abstract

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