Abstract
AbstractA novel 19F 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 1H‐decoupled 19F spectra. These long‐range substituent effects were used to probe the regio‐ and chemoselectivity of stearoyl ACP (acyl carrier protein) Δ9 desaturase‐mediated sulfoxidation. The results clearly demonstrate that mono‐oxygenation of a 10‐thia analogue ACP Δ9 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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