Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase

Amy E. Tremblay; Nigel Tan; Ed Whittle; Derek J. Hodgson; Brian Dawson; Peter H. Buist; John Shanklin

doi:10.1039/b921753c

Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ⁹ desaturase

Amy E. Tremblay
, Nigel Tan
, Ed Whittle
, Derek J. Hodgson
, Brian Dawson
, Peter H. Buist
, John Shanklin

Biochemistry and Cell Biology

Carleton University
Brookhaven National Laboratory
Health Canada

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

4 Scopus citations

Abstract

The stereochemistry of castor stearoyl-ACP Δ⁹ desaturase-mediated 10-sulfoxidation has been determined. This was accomplished by ¹⁹F NMR analysis of a fluorine-tagged product, 18-fluoro-10-thiastearoyl ACP S-oxide, in combination with a chiral solvating agent, (R)-AMA. Sulfoxidation proceeds with the same stereoselectivity as hydrogen removal from the parent stearoyl substrate. These data validate the use of thia probes to determine the stereochemistry and cryptoregiochemistry of desaturase-mediated oxidations.

Original language	English
Pages (from-to)	1322-1328
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	6
DOIs	https://doi.org/10.1039/b921753c
State	Published - 2010

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title = "Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase",

abstract = "The stereochemistry of castor stearoyl-ACP Δ9 desaturase-mediated 10-sulfoxidation has been determined. This was accomplished by 19F NMR analysis of a fluorine-tagged product, 18-fluoro-10-thiastearoyl ACP S-oxide, in combination with a chiral solvating agent, (R)-AMA. Sulfoxidation proceeds with the same stereoselectivity as hydrogen removal from the parent stearoyl substrate. These data validate the use of thia probes to determine the stereochemistry and cryptoregiochemistry of desaturase-mediated oxidations.",

author = "Tremblay, \{Amy E.\} and Nigel Tan and Ed Whittle and Hodgson, \{Derek J.\} and Brian Dawson and Buist, \{Peter H.\} and John Shanklin",

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T1 - Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase

AU - Tremblay, Amy E.

AU - Tan, Nigel

AU - Whittle, Ed

AU - Hodgson, Derek J.

AU - Dawson, Brian

AU - Buist, Peter H.

AU - Shanklin, John

PY - 2010

Y1 - 2010

N2 - The stereochemistry of castor stearoyl-ACP Δ9 desaturase-mediated 10-sulfoxidation has been determined. This was accomplished by 19F NMR analysis of a fluorine-tagged product, 18-fluoro-10-thiastearoyl ACP S-oxide, in combination with a chiral solvating agent, (R)-AMA. Sulfoxidation proceeds with the same stereoselectivity as hydrogen removal from the parent stearoyl substrate. These data validate the use of thia probes to determine the stereochemistry and cryptoregiochemistry of desaturase-mediated oxidations.

AB - The stereochemistry of castor stearoyl-ACP Δ9 desaturase-mediated 10-sulfoxidation has been determined. This was accomplished by 19F NMR analysis of a fluorine-tagged product, 18-fluoro-10-thiastearoyl ACP S-oxide, in combination with a chiral solvating agent, (R)-AMA. Sulfoxidation proceeds with the same stereoselectivity as hydrogen removal from the parent stearoyl substrate. These data validate the use of thia probes to determine the stereochemistry and cryptoregiochemistry of desaturase-mediated oxidations.

UR - https://www.scopus.com/pages/publications/77749344422

U2 - 10.1039/b921753c

DO - 10.1039/b921753c

M3 - Article

C2 - 20204203

AN - SCOPUS:77749344422

SN - 1477-0520

VL - 8

SP - 1322

EP - 1328

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ⁹ desaturase

Abstract

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