Identification of a metagenome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols

Robert Kourist; Sajja Hari Krishna; Jesal S Patel; Flash Bartnek; Timothy S Hitchman; David P Weiner; Uwe T Bornscheuer

doi:10.1039/b709965g

Identification of a metagenome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols

Robert Kourist, Sajja Hari Krishna, Jesal S Patel, Flash Bartnek, Timothy S Hitchman, David P Weiner, Uwe T Bornscheuer

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

Abstract

35 metagenome-derived esterases bearing a GGG(A)X motif were screened for activity and enantioselectivity in the hydrolysis of a range of tertiary alcohol acetates. Most of the active esterases showed little or no enantioselectivity in the hydrolysis of the terpinyl acetate, linalyl acetate and 3-methylpent-1-yn-3-yl acetate. However, one esterase showed excellent enantioselectivity (E > 100) in the kinetic resolution of 1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate as confirmed by a preparative scale reaction.

Original language	English
Pages (from-to)	3310-3313
Number of pages	4
Journal	Organic & Biomolecular Chemistry
Volume	5
Issue number	20
DOIs	https://doi.org/10.1039/b709965g
Publication status	Published - 2007
Externally published	Yes

Keywords

Acetates
Esterases
Gene Library
Genome
Kinetics
Journal Article
Research Support, Non-U.S. Gov't

Fields of Expertise

Human- & Biotechnology

Access to Document

10.1039/b709965g

Cite this

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title = "Identification of a metagenome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols",

abstract = "35 metagenome-derived esterases bearing a GGG(A)X motif were screened for activity and enantioselectivity in the hydrolysis of a range of tertiary alcohol acetates. Most of the active esterases showed little or no enantioselectivity in the hydrolysis of the terpinyl acetate, linalyl acetate and 3-methylpent-1-yn-3-yl acetate. However, one esterase showed excellent enantioselectivity (E > 100) in the kinetic resolution of 1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate as confirmed by a preparative scale reaction.",

keywords = "Acetates, Esterases, Gene Library, Genome, Kinetics, Journal Article, Research Support, Non-U.S. Gov't",

author = "Robert Kourist and {Hari Krishna}, Sajja and Patel, {Jesal S} and Flash Bartnek and Hitchman, {Timothy S} and Weiner, {David P} and Bornscheuer, {Uwe T}",

year = "2007",

doi = "10.1039/b709965g",

language = "English",

volume = "5",

pages = "3310--3313",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "20",

}

TY - JOUR

T1 - Identification of a metagenome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols

AU - Kourist, Robert

AU - Hari Krishna, Sajja

AU - Patel, Jesal S

AU - Bartnek, Flash

AU - Hitchman, Timothy S

AU - Weiner, David P

AU - Bornscheuer, Uwe T

PY - 2007

Y1 - 2007

N2 - 35 metagenome-derived esterases bearing a GGG(A)X motif were screened for activity and enantioselectivity in the hydrolysis of a range of tertiary alcohol acetates. Most of the active esterases showed little or no enantioselectivity in the hydrolysis of the terpinyl acetate, linalyl acetate and 3-methylpent-1-yn-3-yl acetate. However, one esterase showed excellent enantioselectivity (E > 100) in the kinetic resolution of 1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate as confirmed by a preparative scale reaction.

AB - 35 metagenome-derived esterases bearing a GGG(A)X motif were screened for activity and enantioselectivity in the hydrolysis of a range of tertiary alcohol acetates. Most of the active esterases showed little or no enantioselectivity in the hydrolysis of the terpinyl acetate, linalyl acetate and 3-methylpent-1-yn-3-yl acetate. However, one esterase showed excellent enantioselectivity (E > 100) in the kinetic resolution of 1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate as confirmed by a preparative scale reaction.

KW - Acetates

KW - Esterases

KW - Gene Library

KW - Genome

KW - Kinetics

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1039/b709965g

DO - 10.1039/b709965g

M3 - Article

C2 - 17912383

SN - 1477-0520

VL - 5

SP - 3310

EP - 3313

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 20

ER -

Identification of a metagenome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols

Abstract

Keywords

Fields of Expertise

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