Biosynthesis and characterization of a series of deuterated cis,cis-octadeca-6,9-dienoic acids.

Abstract:

:[4,4-2H2]-, [5,5-2H2)-, [6-2H]-, [7-2H]-, [8,8-2H2)-, [11,11-2H2]-, [14,14-2H2]- and [18,18,18-2H3]-cis,cis-octadeca-6,9-dienoic (isolinoleic) acid were synthesized by supplementing cultures of the protozoan Tetrahymena with the corresponding deuterated cis-octadeca-9-enoic (oleic) acids. The cultures were harvested, the deuterated isolinoleic acids isolated and analyzed for purity by GC and TLC, and the structure and the level and position of deuteration of each fatty acid determined by 13C-NMR spectroscopy. The 13C resonances of all 18 carbons were also assigned based upon alpha-carbon deuterium isotope shifts and by comparison of the spectra to those of other polyunsaturated fatty acids. The results illustrate the utility of a biological approach for the synthesis of deuterated polyunsaturated fatty acids in yields suitable for 2H-NMR studies of membranes and possibly human metabolism.

journal_name

Chem Phys Lipids

authors

Baenziger JE,Smith IC,Hill RJ

doi

10.1016/0009-3084(90)90055-v

subject

Has Abstract

pub_date

1990-04-01 00:00:00

pages

17-23

issue

1

eissn

0009-3084

issn

1873-2941

pii

0009-3084(90)90055-V

journal_volume

54

pub_type

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