The synthesis of optically pure enantiomers of N-acyl-homoserine lactone autoinducers and their analogues

被引:42
作者
Ikeda, T [1 ]
Kajiyama, K [1 ]
Kita, T [1 ]
Takiguchi, N [1 ]
Kuroda, A [1 ]
Kato, J [1 ]
Ohtake, H [1 ]
机构
[1] Hiroshima Univ, Dept Fermentat Technol, Hiroshima 7398527, Japan
关键词
D O I
10.1246/cl.2001.314
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Optically pure enantiomers of N-acyl-homoserine lactones and thiolactones, whose optical purities were unambiguously determined by chiral stationary phase HPLC analyses, were firstly synthesized. Bioassays revealed that L-isomers were essential as the autoinducers in quorum sensing, while no effect was observed with D-isomers.
引用
收藏
页码:314 / 315
页数:2
相关论文
共 10 条
[1]   AUTOREGULATION OF CARBAPENEM BIOSYNTHESIS IN ERWINIA-CAROTOVORA BY ANALOGS OF N-(3-OXOHEXANOYL)-L-HOMOSERINE LACTONE [J].
CHHABRA, SR ;
STEAD, P ;
BAINTON, NJ ;
SALMOND, GPC ;
STEWART, GSAB ;
WILLIAMS, P ;
BYCROFT, BW .
JOURNAL OF ANTIBIOTICS, 1993, 46 (03) :441-454
[2]  
Greenberg EP, 1997, ASM NEWS, V63, P371
[3]   Quorum sensing and Chromobacterium violaceum:: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones [J].
McClean, KH ;
Winson, MK ;
Fish, L ;
Taylor, A ;
Chhabra, SR ;
Camara, M ;
Daykin, M ;
Lamb, JH ;
Swift, S ;
Bycroft, BW ;
Stewart, GSAB ;
Williams, P .
MICROBIOLOGY-UK, 1997, 143 :3703-3711
[4]  
Miller J. H., 1972, EXPT MOL GENETICS
[5]   Regulation of las and rhl quorum sensing in Pseudomonas aeruginosa [J].
Pesci, EC ;
Pearson, JP ;
Seed, PC ;
Iglewski, BH .
JOURNAL OF BACTERIOLOGY, 1997, 179 (10) :3127-3132
[6]   Quorum sensing in Vibrio fischeri: Probing autoinducer-LuxR interactions with autoinducer analogs [J].
Schaefer, AL ;
Hanzelka, BL ;
Eberhard, A ;
Greenberg, EP .
JOURNAL OF BACTERIOLOGY, 1996, 178 (10) :2897-2901
[7]   Identification of genes controlled by quorum sensing in Pseudomonas aeruginosa [J].
Whiteley, M ;
Lee, KM ;
Greenberg, EP .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (24) :13904-13909
[8]  
Williams P, 1996, MOLECULAR BIOLOGY OF PSEUDOMONADS, P195
[9]   MULTIPLE N-ACYL-L-HOMOSERINE LACTONE SIGNAL MOLECULES REGULATE PRODUCTION OF VIRULENCE DETERMINANTS AND SECONDARY METABOLITES IN PSEUDOMONAS-AERUGINOSA [J].
WINSON, MK ;
CAMARA, M ;
LATIFI, A ;
FOGLINO, M ;
CHHABRA, SR ;
DAYKIN, M ;
BALLY, M ;
CHAPON, V ;
SALMOND, GPC ;
BYCROFT, BW ;
LAZDUNSKI, A ;
STEWART, GSAB ;
WILLIAMS, P .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (20) :9427-9431
[10]   AGROBACTERIUM CONJUGATION AND GENE-REGULATION BY N-ACYL-L-HOMOSERINE LACTONES [J].
ZHANG, LH ;
MURPHY, PJ ;
KERR, A ;
TATE, ME .
NATURE, 1993, 362 (6419) :446-448