Synthesis of methyl (5Z,8Z,11Z,14Z,17Z)- and (5Z,8Z,11Z,14Z,17E)-[18-14C] eicosapentaenoate

被引：0
作者：
Eynard, T
Poullain, D
Vatele, JM
Noel, JP
Chardigny, JM
Sebedio, JL
机构：
[1] Univ Claude Bernard, CNRS, Lab Chim Organ 1, CPE Lyon, F-69622 Villeurbanne, France
[2] CEA Saclay, Serv Mol Marquees, F-91191 Gif Sur Yvette, France
[3] INRA, Unite Nutr Lipidique, F-21034 Dijon, France
来源：
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 1998年 / 41卷 / 05期
关键词：
n-3 labelled fatty acids; Wittig reaction;
D O I：
10.1002/(SICI)1099-1344(199805)41:5<411::AID-JLCR94>3.0.CO;2-7
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
In order to have a better insight of the effect of the double bond geometry of EPA on its anti-aggregating properties, methyl ester of [18-C-14] EPA and of its Delta 17t isomer were synthesized from a common intermediate [(3Z,6Z,9Z)-12,12-diethoxydodeca-3,6,9-trienyl]triphenylphosphonium iodide 11 via three sequential Wittig olelination. Labelled methyl ester of EPA 16b and EPA Delta 17t 17b were obtained in near 100% isomeric and radiochemical purities.
引用
收藏
页码：411 / 421
页数：11
相关论文
共 26 条
  • [1] ACKMAN RG, 1974, J AM OIL CHEM SOC, V51, P42, DOI 10.1007/BF00000011
  • [2] HYDROGENATION OF FATTY ACIDS TO ALCOHOLS
    ADAMS, PT
    SELFF, RE
    TOLBERT, BM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (09) : 2416 - 2417
  • [3] STEREOCHEMICAL CONTROL IN WITTIG OLEFIN SYNTHESIS - PREPARATION OF PINK BOLLWORM SEX-PHEROMONE MIXTURE, GOSSYPLURE
    ANDERSON, RJ
    HENRICK, CA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (15) : 4327 - 4334
  • [4] BARBOT F, 1981, J CHEM RES-S, P343
  • [5] BERLAGE U, 1987, TETRAHEDRON LETT, V27, P3091
  • [6] CHARDIGNY JM, 1995, EUR J CLIN NUTR, V49, P523
  • [7] EFFECTS OF TRANS N-3 POLYUNSATURATED FATTY-ACIDS ON HUMAN PLATELET-AGGREGATION
    CHARDIGNY, JM
    SEBEDIO, JL
    JUANEDA, P
    VATELE, JM
    GRANDGIRARD, A
    [J]. NUTRITION RESEARCH, 1995, 15 (10) : 1463 - 1471
  • [8] OCCURRENCE OF N-3 TRANSPOLYUNSATURATED FATTY-ACIDS IN HUMAN PLATELETS
    CHARDIGNY, JM
    SEBEDIO, JL
    JUANEDA, P
    VATELE, JM
    GRANDGIRARD, A
    [J]. NUTRITION RESEARCH, 1993, 13 (10) : 1105 - 1111
  • [9] Identification of novel trans isomers of 20:5n-3 in liver lipids of rats fed a heated oil
    Chardigny, JM
    Sebedio, JL
    Grandgirard, A
    Martine, L
    Berdeaux, O
    Vatele, JM
    [J]. LIPIDS, 1996, 31 (02) : 165 - 168
  • [10] TRANS FATTY-ACID ISOMERS IN CANADIAN HUMAN-MILK
    CHEN, ZY
    PELLETIER, G
    HOLLYWOOD, R
    RATNAYAKE, WMN
    [J]. LIPIDS, 1995, 30 (01) : 15 - 21
123