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ω ‐Fluoro Thiafatty Acids: New Mechanistic Probes of Desaturase‐Mediated Reactions
Author(s) -
Hodgson Derek J.,
Lao Kim Y. Y.,
Dawson Brian,
Buist Peter H.
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390312
Subject(s) - chemistry , substrate (aquarium) , sulfoxide , yeast , stereochemistry , in vitro , biochemistry , organic chemistry , oceanography , geology
A series of 18‐fluoro thiastearates were prepared and incubated with a yeast Δ9‐desaturating system. The relative efficiency of desaturase‐mediated sulfoxidation was monitored via 19 F‐NMR analysis of the sulfoxide products, and a strong preference for oxo transfer to the S‐atom occupying the 9‐position was confirmed. The oxidation profile obtained in this manner matched that of analogous experiments with non‐fluorinated substrates. These results form the basis of a versatile 19 F‐NMR‐based method for mapping the position of the putative diiron oxidant relative to substrate, and has potential application to the study of membrane‐bound desaturases in vitro.