Synthesis of the four stereoisomers of 2,6-dimethyloctane-1,8-dioic acid, a component of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatus

被引：19

作者：

Nakai, T

Yajima, A

Akasaka, K

Kaihoku, T

Ohtaki, M

Nukada, T

Ohrui, H

Yabuta, G

机构：

[1] Tokyo Univ Agr, Fac Appl Biol Sci, Dept Fermentat Sci, Setagaya Ku, Tokyo 1568502, Japan

[2] Tohoku Univ, Grad Sch Life Sci, Aoba Ku, Sendai, Miyagi 9818555, Japan

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2005年 / 69卷 / 12期

关键词：

copulation release pheromone; cowpea weevil; Callosobruchus maculatus; 2-(2,3-anthhracenedicarboximide)-l-cyclohexyl ester;

D O I：

10.1271/bbb.69.2401

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A diastereomeric mixture and the four stereoisomers of 2,6-dimethyloctane-1,8-dioic acid (2), a copulation release pheromone of the cowpea weevil, Callosobruchus inaculatus, were synthesized. The stereoisomeric purities of the four synthetic isomers of 2 were determined by the HPLC analyses of their bis-2-(2,3-anthracenedicarboximide)-1-cyclohexyl esters.

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页码：2401 / 2408

页数：8

相关论文

共 27 条

[1] PHEROMONE SYNTHESIS .146. SYNTHESIS OF (R)-CALLOSOBRUCHUSIC ACID FROM METHYL (R)-3-CARBOXYBUTANOATE [J].

ABO, M ;

MORI, K .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (02) :265-267

[2] Highly sensitive isomeric determination of beraprost sodium in plasma using a fluorescent chiral derivatization reagent [J].

Akasaka, K ;

Ohrui, H ;

Meguro, H ;

Umestu, T .

ANALYTICAL SCIENCES, 1997, 13 :461-466

[3] DETERMINATION OF CARBOXYLIC-ACIDS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY WITH 2-(2,3-ANTHRACENEDICARBOXIMIDO)ETHYL TRIFLUOROMETHANESULFONATE AS A HIGHLY SENSITIVE FLUORESCENT LABELING REAGENT [J].

AKASAKA, K ;

OHRUI, H ;

MEGURO, H .

ANALYST, 1993, 118 (07) :765-768

[4]

Akasaka K, 1999, BUNSEKI KAGAKU, V48, P1085

[5]

Akasaka K, 1998, ENANTIOMER, V3, P169

[6] Enantiomeric separation of carboxylic acids having chiral centers remote from the carboxyl group by labelling with a chiral fluorescent derivatization reagent [J].

Akasaka, K ;

Meguro, H ;

Ohrui, H .

TETRAHEDRON LETTERS, 1997, 38 (39) :6853-6856

[7] Enatiomeric separation of branched fatty acids after conversion with trans-2-(2,3-anthracenedicarboximido)cyclohexanol, a highly sensitive chiral fluorescent conversion reagent [J].

Akasaka, K ;

Ohrui, H .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1999, 63 (07) :1209-1215

[8] ASYMMETRIC GLYCINE ENOLATE ALDOL REACTIONS - SYNTHESIS OF CYCLOSPORINES UNUSUAL AMINO-ACID, MEBMT [J].

EVANS, DA ;

WEBER, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6757-6761

[9] SYNTHESIS OF THE CYCLIC HEXAPEPTIDE ECHINOCANDIN-D - NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY ALPHA-AMINO-ACIDS [J].

EVANS, DA ;

WEBER, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7151-7157

[10] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739