Probing substrate-product relationships by natural abundance deuterium 2D NMR spectroscopy in liquid-crystalline solvents: epoxidation of linoleate to vernoleate by two different plant enzymes

Analytical and Bioanalytical Chemistry
I BillaultRichard J Robins

Abstract

Natural abundance deuterium 2D NMR spectroscopy in weakly ordering, polypeptide chiral liquid crystals is a powerful technique that enables determination of enantiotopic isotopic ratios ((2)H/(1)H)( i ) at the methylene groups of long-chain fatty acids. This technique has been used to study the bioconversion of linoleic acid to vernoleic acid with the objective of establishing the in-vivo site-specific fractionation of (2)H associated with this process. The fractionation pattern was investigated in Euphorbia lagascae and Vernonia galamensis, plants that use different enzyme systems to perform the Δ(12)-epoxidation: a cytochrome P450 monooxygenase in the former and a di-iron dioxygenase in the latter. The specific interest in this study was to ascertain whether different ((2)H/(1)H)( i ) isotopic ratios in substrate and product might reflect distinct features of the nature of the reaction centre. However, both the linoleate (substrate) samples and both vernoleate (product) samples isolated from the seed oils of the two plants had remarkably similar (2)H isotope profiles, with selection against (2)H in the positions around the Δ(12)-epoxidation site. This is interpreted as indicating that, despite differences in the form in which...Continue Reading

References

May 15, 1978·Biochemical Pharmacology·R P Hanzlik, G O Shearer
Oct 9, 1998·Progress in Lipid Research·E Blée
Aug 14, 1999·The Journal of Biological Chemistry·A R Brash
Aug 31, 2002·Chembiochem : a European Journal of Chemical Biology·Jia-Rong DuanRichard Robins
Nov 5, 2002·Current Opinion in Chemical Biology·Behnaz Behrouzian, Peter H Buist
Oct 12, 2004·Phytochemistry·Gérard J MartinMaryvonne L Martin
Sep 17, 2008·Bioorganic & Medicinal Chemistry Letters·Cyril JacquotWilfred A van der Donk

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Citations

Feb 13, 2018·Plant Reproduction·Sébastien Baud
Jan 4, 2013·Magnetic Resonance in Chemistry : MRC·Philippe LesotIsabelle Billault
Mar 5, 2020·Progress in Nuclear Magnetic Resonance Spectroscopy·Philippe LesotOlivier Lafon

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