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Use of 19F NMR spectroscopy to probe enzymatic oxidation of fluorine-tagged sulfides

✍ Scribed by Behnaz Behrouzian; Derek Hodgson; Christopher K. Savile; Brian Dawson; Peter H. Buist; John Shanklin

Book ID
102523971
Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
112 KB
Volume
40
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

A novel ^19^F NMR‐based method for monitoring the enzymatic oxidation of thia fatty acid analogues is presented. Our approach is based on the observation that methyl ω‐monofluorinated 9‐thia‐ and 10‐thiaoctadecanoates and their S‐oxide and S‐dioxide derivatives are easily distinguishable via their ^1^H‐decoupled ^19^F spectra. These long‐range substituent effects were used to probe the regio‐ and chemoselectivity of stearoyl ACP (acyl carrier protein) Δ^9^ desaturase‐mediated sulfoxidation. The results clearly demonstrate that mono‐oxygenation of a 10‐thia analogue ACP Δ^9^ desaturase was more efficient than that of a 9‐thia substrate. A product previously undetected by TLC was observed for the first time in the product mixture obtained from 18‐fluoro‐9‐thiaoctadecanoyl‐ACP. Copyright © 2002 John Wiley & Sons, Ltd.

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