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Natural Deuterium Distribution in Long‐Chain Fatty Acids Is Nonstatistical: A Site‐Specific Study by Quantitative 2 H NMR Spectroscopy

Natural Deuterium Distribution in Long‐Chain Fatty Acids Is Nonstatistical: A Site‐Specific Study... Quantitative 2H NMR spectroscopy has been used to study the site‐specific natural occurrence of 2H in common unsaturated fatty acids. A marked nonstatistical isotopic distribution of 2H is observed in both methyl oleate and methyl linoleate. By chemical modification, the internal isotopic 2H signatures of these products have been partially accessed. Notably, it can be seen that (1) the sites of desaturation show a strong impoverishment at only one ethylenic position of each desaturation; (2) the level of impoverishment reflects the source of the hydrogen atoms present; and (3) a gradient of 2H content occurs along the chain. These effects can in part be related to the mechanisms proposed for the enzymes responsible for the various steps of biosynthesis of unsaturated fatty acids in plants. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png ChemBioChem Wiley

Natural Deuterium Distribution in Long‐Chain Fatty Acids Is Nonstatistical: A Site‐Specific Study by Quantitative 2 H NMR Spectroscopy

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References (20)

Publisher
Wiley
Copyright
© 2001 WILEY‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
ISSN
1439-4227
eISSN
1439-7633
DOI
10.1002/1439-7633(20010601)2:6<425::AID-CBIC425>3.0.CO;2-Z
Publisher site
See Article on Publisher Site

Abstract

Quantitative 2H NMR spectroscopy has been used to study the site‐specific natural occurrence of 2H in common unsaturated fatty acids. A marked nonstatistical isotopic distribution of 2H is observed in both methyl oleate and methyl linoleate. By chemical modification, the internal isotopic 2H signatures of these products have been partially accessed. Notably, it can be seen that (1) the sites of desaturation show a strong impoverishment at only one ethylenic position of each desaturation; (2) the level of impoverishment reflects the source of the hydrogen atoms present; and (3) a gradient of 2H content occurs along the chain. These effects can in part be related to the mechanisms proposed for the enzymes responsible for the various steps of biosynthesis of unsaturated fatty acids in plants.

Journal

ChemBioChemWiley

Published: Jun 1, 2001

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