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

被引:17
作者
Dekhane, M
Douglas, KT
Gilbert, P
机构
[1] Department of Pharmacy, University of Manchester, Manchester
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.
引用
收藏
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
    BAINTON, NJ
    STEAD, P
    CHHABRA, SR
    BYCROFT, BW
    SALMOND, GPC
    STEWART, GSAB
    WILLIAMS, P
    [J]. BIOCHEMICAL JOURNAL, 1992, 288 : 997 - 1004
  • [2] BIOSYNTHESIS AND STEREOCHEMISTRY OF THE AUTOINDUCER CONTROLLING LUMINESCENCE IN VIBRIO-HARVEYI
    CAO, JG
    MEIGHEN, EA
    [J]. 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
    EBERHARD, A
    BURLINGAME, AL
    EBERHARD, C
    KENYON, GL
    NEALSON, KH
    OPPENHEIMER, NJ
    [J]. 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
    GAMBELLO, MJ
    KAYE, S
    IGLEWSKI, BH
    [J]. 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
    PEARSON, JP
    GRAY, KM
    PASSADOR, L
    TUCKER, KD
    EBERHARD, A
    IGLEWSKI, BH
    GREENBERG, EP
    [J]. 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
    WIERENGA, W
    SKULNICK, HI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (02) : 310 - 311
  • [10] WILLIAMS P, 1992, FEMS MICROBIOL LETT, V100, P161