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In vitro enzymatic oxidation of a fluorine-tagged sulfido substrate analogue: a 19F NMR investigation

✍ Scribed by Amy E. Tremblay; Peter H. Buist; Derek Hodgson; Brian Dawson; Ed Whittle; John Shanklin

Book ID
102524772
Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
129 KB
Volume
44
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^1^H‐decoupled ^19^F NMR has been used to monitor the highly regioselective oxidation of a fluorine‐tagged thia‐fatty acid derivative by castor stearoyl‐ACP Δ^9^ desaturase. The major enzymatic product, after reductive work‐up, was identified as 9‐fluoro‐1‐nonanol. This compound could be easily distinguished from substrate and a 9‐sulfoxy by‐product on the basis of its ^19^F NMR chemical shift and spiking experiments using authentic standards. Structural assignment of the cleavage product was confirmed by GC‐MS analysis of the enzymatic products. Copyright © 2006 John Wiley & Sons, Ltd.

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