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Title: Stereochemistry of 10-sulfoxidation catalyzed by a soluble delta9 desaturase

Abstract

The stereochemistry of castor stearoyl-ACP 9 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.

Authors:
; ; ; ; ; ;
Publication Date:
Research Org.:
Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Org.:
Doe - Office Of Science
OSTI Identifier:
983859
Report Number(s):
BNL-91158-2010-JA
Journal ID: ISSN 1477-0520; R&D Project: BO-059; KC0304000; TRN: US201014%%1851
DOE Contract Number:  
DE-AC02-98CH10886
Resource Type:
Journal Article
Journal Name:
Organic & Biomolecular Chemistry
Additional Journal Information:
Journal Volume: 8; Journal Issue: 6; Journal ID: ISSN 1477-0520
Country of Publication:
United States
Language:
English
Subject:
08 HYDROGEN; 59 BASIC BIOLOGICAL SCIENCES; 99 GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE; BEAMS; CASTOR; DATA; HYDROGEN; NUCLEAR MAGNETIC RESONANCE; REMOVAL; STEREOCHEMISTRY; USES

Citation Formats

Tremblay, A E, Shanklin, J, Tan, N, Whittle, E, Hodgson, D J, Dawson, B, and Buist, P H. Stereochemistry of 10-sulfoxidation catalyzed by a soluble delta9 desaturase. United States: N. p., 2010. Web. doi:10.1039/b921753c.
Tremblay, A E, Shanklin, J, Tan, N, Whittle, E, Hodgson, D J, Dawson, B, & Buist, P H. Stereochemistry of 10-sulfoxidation catalyzed by a soluble delta9 desaturase. United States. https://doi.org/10.1039/b921753c
Tremblay, A E, Shanklin, J, Tan, N, Whittle, E, Hodgson, D J, Dawson, B, and Buist, P H. 2010. "Stereochemistry of 10-sulfoxidation catalyzed by a soluble delta9 desaturase". United States. https://doi.org/10.1039/b921753c.
@article{osti_983859,
title = {Stereochemistry of 10-sulfoxidation catalyzed by a soluble delta9 desaturase},
author = {Tremblay, A E and Shanklin, J and Tan, N and Whittle, E and Hodgson, D J and Dawson, B and Buist, P H},
abstractNote = {The stereochemistry of castor stearoyl-ACP 9 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.},
doi = {10.1039/b921753c},
url = {https://www.osti.gov/biblio/983859}, journal = {Organic & Biomolecular Chemistry},
issn = {1477-0520},
number = 6,
volume = 8,
place = {United States},
year = {Sun Mar 21 00:00:00 EDT 2010},
month = {Sun Mar 21 00:00:00 EDT 2010}
}