Synthesis of (S)-(+)-enantiomers of food-relevant (n-5)-monoenoic and saturated anteiso-fatty acids by a Wittig reaction

被引：23

作者：

Thurnhofer, Saskia ^{[1
]}

Vetter, Walter ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Food Chem, D-70599 Stuttgart, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 05期

关键词：

methyl branched fatty acids; anteiso-fatty acids; monoenoic anteiso-fatty acids; Wittig reaction; enantioselective synthesis; silver-ion chromatography;

D O I：

10.1016/j.tet.2006.11.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed an enantioselective synthesis for the food-relevant anteiso-fatty acids a15:0, a16:0, and a17:0. Different (carboxyalkyl)triphenylphosphonium bromide salts were coupled with (S)-3-methylpentanal in a Wittig reaction. Mixtures of the obtained cis-/trans-isomers were separated by Ag+-HPLC to give the novel cis-isomers of (S)-(+)-a15:1n-5, (S)-(+)-a16:1n-5, and (S)-(+)-a17:1n-5. Hydrogenation of the monoenoic products led to (S)-(+)-a15:0, (S)-(+)-a16:0, and (S)-(+)-a17:0, which are essential for the assessment of the bioactivity of tests with standards of anteiso-fatty acids. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1140 / 1145

页数：6

共 46 条

[1] ANALYSIS OF THE MONOENOIC FATTY-ACID DISTRIBUTION IN HYDROGENATED VEGETABLE-OILS BY SILVER-ION HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

ADLOF, RO ;

COPES, LC ;

EMKEN, EA .

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1995, 72 (05) :571-574

[2] Absolute configuration of a ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate, Coolia monotis [J].

Akasaka, K ;

Shichijyukari, S ;

Matsuoka, S ;

Murata, M ;

Meguro, H ;

Ohrui, H .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (09) :1842-1846

[3] Chiral discrimination of branched-chain fatty acids by reversed-phase HPLC after labeling with a chiral fluorescent conversion reagent [J].

Akasaka, K ;

Ohrui, H .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2004, 68 (01) :153-158

[4] Critical role of anteiso-C-15:0 fatty acid in the growth of Listeria monocytogenes at low temperatures [J].

Annous, BA ;

Becker, LA ;

Bayles, DO ;

Labeda, DP ;

Wilkinson, BJ .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1997, 63 (10) :3887-3894

[5] Stereoisomeric flavour compounds - LXXX: alkyl-branched alkanals - stereodifferentiation, structure elucidation and structure-function relationship [J].

Bartschat, D ;

Mosandl, A .

ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG A-FOOD RESEARCH AND TECHNOLOGY, 1998, 206 (03) :165-168

[6]

BERGELSON LD, 1964, ANGEW CHEM, V3, P113

[7] MASS-SPECTROMETRY OF ISO AND ANTI-ISO MONOENOIC FATTY-ACIDS [J].

BOON, JJ ;

VANDEGRAAF, B ;

SCHUYL, PJW ;

DELANGE, F ;

DELEEUW, JW .

LIPIDS, 1977, 12 (09) :717-721

[8] SIGNIFICANCE AND TAXONOMIC VALUE OF ISO AND ANTEISO-MONOENOIC FATTY-ACIDS AND BRANCHED BETA-HYDROXY ACIDS IN DESULFOVIBRIO-DESULFURICANS [J].

BOON, JJ ;

DELEEUW, JW ;

VANDERHOEK, GJ ;

VOSJAN, JH .

JOURNAL OF BACTERIOLOGY, 1977, 129 (03) :1183-1191

[9] Identification and total synthesis of novel fatty acids from the siphonarid limpet Siphonaria denticulata [J].

Carballeira, NM ;

Cruz, H ;

Hill, CA ;

De Voss, JJ ;

Garson, M .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (11) :1426-1429

[10] The fatty acid composition of a Vibrio alginolyticus associated with the alga Cladophora coelothrix, identification of the novel 9-methyl-10-hexadecenoic acid [J].

Carballeira, NM ;

Sostre, A ;

Stefanov, K ;

Popov, S ;

Kujumgiev, A ;

Dimitrova-Konaklieva, S ;

Tosteson, CG ;

Tosteson, TR .

LIPIDS, 1997, 32 (12) :1271-1275

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