Exploring the hydroxylation-dehydrogenation connection: novel catalytic activity of castor stearoyl-ACP Delta(9) desaturase |
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Authors: | Behrouzian Behnaz Savile Christopher K Dawson Brian Buist Peter H Shanklin John |
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Affiliation: | Department of Biology, Brookhaven National Laboratory, Upton, NY 11973, USA. |
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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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