PMID: 11916411Mar 28, 2002Paper

Exploring the hydroxylation-dehydrogenation connection: novel catalytic activity of castor stearoyl-ACP Delta(9) desaturase

Journal of the American Chemical Society
Behnaz BehrouzianJohn Shanklin

Abstract

The novel product profile obtained by incubating chiral fluorinated substrate analogues with castor stearoyl-ACP Delta(9) desaturase has been rationalized through a series of labeling studies. It was found that the introduction of the Z-double bond between C-9 and C-10 of the parent substrate occurs with pro-R enantioselectivity--a result that accounts for the observed stereochemistry of oxidation products derived from (9R)- and (9S)-9-fluorostearoyl-ACP. Oxidation of (9R)-9-fluorostearoyl-ACP occurs via at least two rapidly interchanging substrate conformations in the active site as detected by reaction pathway branching induced by deuteration at C-10 and C-11. Hydroxylation and desaturation of this substrate share the same site of initial oxidative attack.

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Apr 7, 2005·Current Opinion in Chemical Biology·Romas J Kazlauskas
Jan 23, 2003·Prostaglandins, Leukotrienes, and Essential Fatty Acids·Makoto Miyazaki, James M Ntambi
Nov 5, 2002·Current Opinion in Chemical Biology·Behnaz Behrouzian, Peter H Buist
Jul 23, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·David BalcellsOdile Eisenstein
Sep 18, 2008·Proceedings of the National Academy of Sciences of the United States of America·Edward J WhittleJohn Shanklin
Sep 21, 2011·Proceedings of the National Academy of Sciences of the United States of America·Jodie E GuyJohn Shanklin
Dec 11, 2008·American Journal of Physiology. Endocrinology and Metabolism·Chad M Paton, James M Ntambi
Jul 9, 2004·Proceedings of the National Academy of Sciences of the United States of America·Ingo HeilmannJohn Shanklin
Oct 21, 2018·Journal of Cellular Physiology·Vahid HosseiniMasoud Darabi
Mar 6, 2010·Organic & Biomolecular Chemistry·Amy E TremblayJohn Shanklin
Oct 22, 2005·Organic & Biomolecular Chemistry·Frances CarvalhoPeter H Buist
Apr 5, 2007·Organic & Biomolecular Chemistry·Amy E TremblayJohn Shanklin
Nov 4, 2004·Angewandte Chemie·Uwe T Bornscheuer, Romas J Kazlauskas
May 30, 2020·Journal of Molecular Biology·Jiemin ShenMing Zhou
Jul 21, 2004·Accounts of Chemical Research·Brian G FoxCorina E Rogge
Nov 18, 2005·Progress in Lipid Research·Florence BouvierBilal Camara
May 3, 2019·The Journal of Organic Chemistry·Phillip L van der PeetSpencer J Williams
Mar 29, 2003·The Journal of Organic Chemistry·Gemma VillorbinaGemma Fabriàs
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