Literature DB >> 21076635

Chemical synthesis of deuterium-labeled and unlabeled very long chain polyunsaturated fatty acids.

Ghulam M Maharvi1, Albert O Edwards, Abdul H Fauq.   

Abstract

First syntheses of a deuterium-labeled very long C34-containing polyunsaturated fatty acid, C34:5n5.d(2), and three other unlabeled very long chain C30-32-containing polyunsaturated fatty acids are reported here. These syntheses were achieved by coupling chemically modified C22- and C20-containing polyunsaturated fatty acids with carbanions derived from arylalkyl sulfones, followed by sodium amalgam-mediated desulfonylation.

Entities:  

Year:  2010        PMID： 21076635      PMCID： PMC2976573          DOI： 10.1016/j.tetlet.2010.09.139

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  13 in total

Review 1.  Retinal very long-chain PUFAs: new insights from studies on ELOVL4 protein.

Authors:  Martin-Paul Agbaga; Md Nawajes A Mandal; Robert E Anderson
Journal:  J Lipid Res       Date:  2010-03-18       Impact factor: 5.922

2.  Effects of changes in fat, fish, and fibre intakes on death and myocardial reinfarction: diet and reinfarction trial (DART).

Authors:  M L Burr; A M Fehily; J F Gilbert; S Rogers; R M Holliday; P M Sweetnam; P C Elwood; N M Deadman
Journal:  Lancet       Date:  1989-09-30       Impact factor: 79.321

Review 3.  Very-long-chain fatty acids from the animal and plant kingdoms.

Authors:  T Rezanka
Journal:  Prog Lipid Res       Date:  1989       Impact factor: 16.195

4.  A novel gene for autosomal dominant Stargardt-like macular dystrophy with homology to the SUR4 protein family.

Authors:  A O Edwards; L A Donoso; R Ritter
Journal:  Invest Ophthalmol Vis Sci       Date:  2001-10       Impact factor: 4.799

5.  The composition of food consumed by Greenland Eskimos.

Authors:  H O Bang; J Dyerberg; N Hjøorne
Journal:  Acta Med Scand       Date:  1976

Review 6.  A systemic review of the roles of n-3 fatty acids in health and disease.

Authors:  Natalie D Riediger; Rgia A Othman; Miyoung Suh; Mohammed H Moghadasian
Journal:  J Am Diet Assoc       Date:  2009-04

7.  Role of Stargardt-3 macular dystrophy protein (ELOVL4) in the biosynthesis of very long chain fatty acids.

Authors:  Martin-Paul Agbaga; Richard S Brush; Md Nawajes A Mandal; Kimberly Henry; Michael H Elliott; Robert E Anderson
Journal:  Proc Natl Acad Sci U S A       Date:  2008-08-26       Impact factor: 11.205

Review 8.  Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms.

Authors:  Tomás Rezanka; Karel Sigler
Journal:  Prog Lipid Res       Date:  2009-03-29       Impact factor: 16.195

9.  Long and very long chain polyunsaturated fatty acids of the n-6 series in rat seminiferous tubules. Active desaturation of 24:4n-6 to 24:5n-6 and concomitant formation of odd and even chain tetraenoic and pentaenoic fatty acids up to C32.

Authors:  M I Aveldaño; B S Robinson; D W Johnson; A Poulos
Journal:  J Biol Chem       Date:  1993-06-05       Impact factor: 5.157

10.  Retinal pathology and skin barrier defect in mice carrying a Stargardt disease-3 mutation in elongase of very long chain fatty acids-4.

Authors:  Anne McMahon; Igor A Butovich; Nathan L Mata; Martin Klein; Robert Ritter; James Richardson; David G Birch; Albert O Edwards; Wojciech Kedzierski
Journal:  Mol Vis       Date:  2007-02-26       Impact factor: 2.367
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  4 in total

1.  Retinal bioavailability and functional effects of a synthetic very-long-chain polyunsaturated fatty acid in mice.

Authors:  Aruna Gorusupudi; Rameshu Rallabandi; Binxing Li; Ranganathan Arunkumar; J David Blount; Gregory T Rognon; Fu-Yen Chang; Alexander Wade; Steven Lucas; John C Conboy; Jon D Rainier; Paul S Bernstein
Journal:  Proc Natl Acad Sci U S A       Date:  2021-02-09       Impact factor: 11.205

2.  ELOVL4 protein preferentially elongates 20:5n3 to very long chain PUFAs over 20:4n6 and 22:6n3.

Authors:  Man Yu; Aaron Benham; Sreemathi Logan; R Steven Brush; Md Nawajes A Mandal; Robert E Anderson; Martin-Paul Agbaga
Journal:  J Lipid Res       Date:  2011-12-09       Impact factor: 5.922

3.  Total Synthesis of (-)-Bastimolide A: A Showcase for Type I Anion Relay Chemistry.

Authors:  Joshua B Cox; Alex A Kellum; Yiwen Zhang; Bo Li; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-24       Impact factor: 16.823

4.  The Properties and Role of O-Acyl-ω-hydroxy Fatty Acids and Type I-St and Type II Diesters in the Tear Film Lipid Layer Revealed by a Combined Chemistry and Biophysics Approach.

Authors:  Tuomo Viitaja; Jan-Erik Raitanen; Jukka Moilanen; Riku O Paananen; Filip S Ekholm
Journal:  J Org Chem       Date:  2021-03-17       Impact factor: 4.354
  4 in total

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