SYNTHESIS OF NOVEL PHOSPHONATE ANALOG OF KDO AS A TOOL FOR THE DESIGN OF POTENT INHIBITORS FOR LIPOPOLYSACCHARIDE BIOSYNTHESIS

被引:9
作者
SHEFFERDEENOOR, S [1 ]
BELAKHOV, V [1 ]
BAASOV, T [1 ]
机构
[1] TECHNION ISRAEL INST TECHNOL,DEPT CHEM,IL-32000 HAIFA,ISRAEL
关键词
D O I
10.1016/S0040-4039(00)73325-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The new phosphonate analogue 3 of 2-deoxy-beta-Kdo (2) was prepared in a stereospecific manner via intramolecular C-C bond formation. X-Ray structure analysis and NMR studies of the cyclyzation product established the twist-boat conformation of the pyranose ring with alpha-anomeric configuration of the phosphonate linkage.
引用
收藏
页码:5077 / 5080
页数:4
相关论文
共 26 条
  • [1] INHIBITION OF EPSP SYNTHASE BY ANALOGS OF THE TETRAHEDRAL INTERMEDIATE AND OF EPSP
    ALBERG, DG
    LAUHON, CT
    NYFELER, R
    FASSLER, A
    BARTLETT, PA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) : 3535 - 3546
  • [2] CATALYTIC MECHANISM OF 3-DEOXY-D-MANNO-2-OCTULOSONATE-8-PHOSPHATE SYNTHASE - THE USE OF SYNTHETIC ANALOGS TO PROBE THE STRUCTURE OF THE PUTATIVE REACTION INTERMEDIATE
    BAASOV, T
    SHEFFERDEENOOR, S
    KOHEN, A
    JAKOB, A
    BELAKHOV, V
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1993, 217 (03): : 991 - 999
  • [3] ANOMERIC SPECIFICITY OF 3-DEOXY-D-MANNO-2-OCTULOSONATE 8-PHOSPHATE PHOSPHATASE FROM ESCHERICHIA-COLI
    BAASOV, T
    JAKOB, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) : 4972 - 4974
  • [4] A 2-DEOXY ANALOG OF KDO AS THE 1ST INHIBITOR OF THE ENZYME CMP-KDO SYNTHETASE
    CLAESSON, A
    LUTHMAN, K
    GUSTAFSSON, K
    BONDESSON, G
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 143 (03) : 1063 - 1068
  • [5] ANTIBACTERIAL AGENTS SPECIFICALLY INHIBITING LIPOPOLYSACCHARIDE SYNTHESIS
    GOLDMAN, R
    KOHLBRENNER, W
    LARTEY, P
    PERNET, A
    [J]. NATURE, 1987, 329 (6135) : 162 - 164
  • [6] A NEW CLASS OF SYNTHETIC ANTIBACTERIALS ACTING ON LIPOPOLYSACCHARIDE BIOSYNTHESIS
    HAMMOND, SM
    CLAESSON, A
    JANSSON, AM
    LARSSON, LG
    PRING, BG
    TOWN, CM
    EKSTROM, B
    [J]. NATURE, 1987, 327 (6124) : 730 - 732
  • [7] PREPARATION OF NOVEL PYRANOSYL FLUORIDES OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) FEASIBLE FOR SYNTHESIS OF KDO ALPHA-GLYCOSIDES
    IMOTO, M
    KUSUNOSE, N
    MATSUURA, Y
    KUSUMOTO, S
    SHIBA, T
    [J]. TETRAHEDRON LETTERS, 1987, 28 (50) : 6277 - 6280
  • [8] INOUYE M, 1979, BACTERIAL OUTER MEMB
  • [9] KOHLBRENNER WE, 1985, J BIOL CHEM, V260, P4695
  • [10] SYNTHESIS OF ANALOGS OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID (KDO) AS POTENTIAL INHIBITORS OF CMP-KDO SYNTHETASE
    LUTHMAN, K
    CLAESSON, A
    JANSSON, AM
    PRING, BG
    [J]. CARBOHYDRATE RESEARCH, 1987, 166 (02) : 233 - 251