Literature DB >> 8231662

Synthesis of ethyl arachidonate-19,19,20,20-d4 and ethyl dihomo-gamma-linolenate-19,19,20,20-d4.

D L Luthria1, H Sprecher.   

Abstract

Ethyl 5,8,11,14-eicosatetraenoate-19,19,20,20-d4 and ethyl 8,11,14-eicosatrienoate-19,19,20,20-d4 were synthesized by Grignard coupling of the methanesulfonyl ester of 2,5-undecadiyn-1-ol-10,10,11,11-d4 with 5,8-nonadiynoic acid and 8-nonynoic acid, respectively. The coupled products upon Lindlar reduction, followed by the preparation of their ethyl esters, yielded deuteriated ethyl arachidonate and ethyl dihomo-gamma-linolenate, which were completely characterized by 13C and 1H nuclear magnetic resonance and mass spectral analysis.

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Year:  1993        PMID： 8231662     DOI： 10.1007/bf02536242

Source DB:  PubMed          Journal:  Lipids        ISSN： 0024-4201            Impact factor:   1.880


  11 in total

1.  NADPH-dependent reductive metabolism of cis-5 unsaturated fatty acids. A revised pathway for the beta-oxidation of oleic acid.

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2.  Measurement of prostaglandins, thromboxanes, prostacyclin and their metabolites by gas liquid chromatography--mass spectrometry.

Authors:  K Gréen; M Hamberg; B Samuelsson; M Smigel; J C Frölich
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Review 3.  The organic synthesis of unsaturated fatty acids.

Authors:  H Sprecher
Journal:  Prog Chem Fats Other Lipids       Date:  1978

Review 4.  Synthesis, analysis and application of specifically deuterated lipids.

Authors:  A P Tulloch
Journal:  Prog Lipid Res       Date:  1983       Impact factor: 16.195

5.  Synthesis and characterization of [1-(13)C]-and d8-arachidonic acid.

Authors:  U H Do; M G Sundaram; S Ramachandran; R W Bryant
Journal:  Lipids       Date:  1979-09       Impact factor: 1.880

6.  Fatty acids. Part 50. 13C nuclear magnetic resonance studies of olefinic fatty acids and esters.

Authors:  F D Gunstone; M R Polard; C M Scrimgeour; H S Vedanayagam
Journal:  Chem Phys Lipids       Date:  1977-01       Impact factor: 3.329

7.  Total synthesis and spectral characterization of 5,8,14-icosatrienoic acid and 5,11,14-icosatrienoic acid and their acetylenic analogues.

Authors:  R W Evans; H Sprecher
Journal:  Chem Phys Lipids       Date:  1985 Nov-Dec       Impact factor: 3.329

Review 8.  Molecular basis of mitochondrial fatty acid oxidation defects.

Authors:  P M Coates; K Tanaka
Journal:  J Lipid Res       Date:  1992-08       Impact factor: 5.922

9.  The PMR analysis of non-conjugated alkenoic and alkynoic acids and esters.

Authors:  D J Frost; F D Gunstone
Journal:  Chem Phys Lipids       Date:  1975-09       Impact factor: 3.329

10.  NADPH-dependent beta-oxidation of unsaturated fatty acids with double bonds extending from odd-numbered carbon atoms.

Authors:  T E Smeland; M Nada; D Cuebas; H Schulz
Journal:  Proc Natl Acad Sci U S A       Date:  1992-08-01       Impact factor: 11.205
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  3 in total

1.  Regulation of the biosynthesis of 4,7,10,13,16-docosapentaenoic acid.

Authors:  B S Mohammed; D L Luthria; S P Bakousheva; H Sprecher
Journal:  Biochem J       Date:  1997-09-01       Impact factor: 3.857

2.  The questionable role of a microsomal delta8 acyl-coA-dependent desaturase in the biosynthesis of polyunsaturated fatty acids.

Authors:  Q Chen; F Q Yin; H Sprecher
Journal:  Lipids       Date:  2000-08       Impact factor: 1.880

Review 3.  High-resolution nuclear magnetic resonance spectroscopy--applications to fatty acids and triacylglycerols.

Authors:  M S Jie; J Mustafa
Journal:  Lipids       Date:  1997-10       Impact factor: 1.880
  3 in total

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