A novel convenient route to the naturally occurring 3-oxoacyl-L-homoserinelactones and related bacterial autoinducers

被引：18

作者：

Dekhane, M

Douglas, KT

Gilbert, P

机构：

[1] Department of Pharmacy, University of Manchester, Manchester

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 11期

关键词：

D O I：

10.1016/0040-4039(96)00142-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The naturally occurring 3-oxohexanoyl-L-homoserinelactone (1a), a bacterial autoinducer, has been prepared in 47 % overall yield by condensing stable 3-oxohexanoic acid (2), prepared by hydrolysis from the corresponding ester (3), with L-homoserinelactone using hydroxybenzotriazole (HOBT) and dicyclohexylcarbodiimide (DCC) in non-aqueous media.

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页码：1883 / 1884

页数：2

相关论文

共 11 条

[1] N-(3-OXOHEXANOYL)-L-HOMOSERINE LACTONE REGULATES CARBAPENEM ANTIBIOTIC PRODUCTION IN ERWINIA-CAROTOVORA [J].

BAINTON, NJ ;

STEAD, P ;

CHHABRA, SR ;

BYCROFT, BW ;

SALMOND, GPC ;

STEWART, GSAB ;

WILLIAMS, P .

BIOCHEMICAL JOURNAL, 1992, 288 :997-1004

[2] BIOSYNTHESIS AND STEREOCHEMISTRY OF THE AUTOINDUCER CONTROLLING LUMINESCENCE IN VIBRIO-HARVEYI [J].

CAO, JG ;

MEIGHEN, EA .

JOURNAL OF BACTERIOLOGY, 1993, 175 (12) :3856-3862

[3]

CAO JG, 1989, J BIOL CHEM, V264, P21670

[4] STRUCTURAL IDENTIFICATION OF AUTOINDUCER OF PHOTOBACTERIUM-FISCHERI LUCIFERASE [J].

EBERHARD, A ;

BURLINGAME, AL ;

EBERHARD, C ;

KENYON, GL ;

NEALSON, KH ;

OPPENHEIMER, NJ .

BIOCHEMISTRY, 1981, 20 (09) :2444-2449

[5] LASR OF PSEUDOMONAS-AERUGINOSA IS A TRANSCRIPTIONAL ACTIVATOR OF THE ALKALINE PROTEASE GENE (APR) AND AN ENHANCER OF EXOTOXIN-A EXPRESSION [J].

GAMBELLO, MJ ;

KAYE, S ;

IGLEWSKI, BH .

INFECTION AND IMMUNITY, 1993, 61 (04) :1180-1184

[6]

KOCH GK, 1974, TETRAHEDRON LETT, V7, P603

[7]

LEWIS N, 1983, TETRAHEDRON LETT, V48, P5425

[8] STRUCTURE OF THE AUTOINDUCER REQUIRED FOR EXPRESSION OF PSEUDOMONAS-AERUGINOSA VIRULENCE GENES [J].

PEARSON, JP ;

GRAY, KM ;

PASSADOR, L ;

TUCKER, KD ;

EBERHARD, A ;

IGLEWSKI, BH ;

GREENBERG, EP .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (01) :197-201

[9] GENERAL, EFFICIENT, ONE-STEP SYNTHESIS OF BETA-KETO-ESTERS [J].

WIERENGA, W ;

SKULNICK, HI .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (02) :310-311

[10]

WILLIAMS P, 1992, FEMS MICROBIOL LETT, V100, P161