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

Magnetic Resonance in Chemistry : MRC
Amy E TremblayJohn Shanklin

Abstract

1H-decoupled 19F NMR has been used to monitor the highly regioselective oxidation of a fluorine-tagged thia-fatty acid derivative by castor stearoyl-ACP delta9 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 19F 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.

References

Jan 23, 2003·Prostaglandins, Leukotrienes, and Essential Fatty Acids·P SperlingE Heinz
Mar 12, 2004·Annual Review of Plant Physiology and Plant Molecular Biology·John Shanklin, Edgar B. Cahoon
Mar 26, 2004·Natural Product Reports·Peter H Buist

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Citations

Mar 6, 2010·Organic & Biomolecular Chemistry·Amy E TremblayJohn Shanklin
Apr 5, 2007·Organic & Biomolecular Chemistry·Amy E TremblayJohn Shanklin

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