SYNTHESIS OF (PLUS-OR-MINUS) MYO-INOSITOL-1-O-METHYLPHOSPHONATE-4,5-BIS(PHOSPHATE), AN ANALOG OF D-MYO-INOSITOL-1,4,5-TRIS(PHOSPHATE)

被引:6
|
作者
SCHMITT, L [1 ]
SPIESS, B [1 ]
SCHLEWER, G [1 ]
机构
[1] FAC PHARM STRASBOURG,PHARMACOCHIM MOLEC LAB,74 ROUTE RHIN,F-67401 ILLKIRCH GRAFFENS,FRANCE
关键词
D O I
10.1016/S0040-4039(00)61597-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of (+/-)myo-inositol-1-Ounderbar-methylphosphonate-4,5-bis(phosphate) is reported. This compound is an analogue of D-myo-inositol-1,4,5-tris(phosphate) in which the phosphate group in position 1 is replaced by a methyl phosphonate function and where the important vicinal phosphate groups in positions 4 and 5 am preserved.
引用
收藏
页码:7059 / 7060
页数:2
相关论文
共 50 条
  • [1] Rapid synthesis and properties of (+/-)-6-deoxy-6-fluoro-myo-inositol-1,4,5-tris(phosphate) an analogue of myo-inositol-1,4,5-tris(phosphate).
    Guedat, P
    Poitras, M
    Spiess, B
    Guillemette, G
    Schlewer, G
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (10) : 1175 - 1178
  • [2] SYNTHESIS AND SOME PROPERTIES OF D-MYO-INOSITOL 1,4,5-TRIS(DIHYDROGEN PHOSPHATE)
    OZAKI, S
    KONDO, Y
    SHIOTANI, N
    OGASAWARA, T
    WATANABE, Y
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (06): : 729 - 737
  • [3] Synthesis of (±)-2-O-[4'-(N-9′′-purinyl)butyl myo-inositol 1,4,5-tris(phosphate), a potent full agonist at the D-myo-inositol 1,4,5-tris(phosphate) receptor
    Moris, MA
    Caron, AZ
    Guillemette, G
    Rognan, D
    Schmitt, M
    Schlewer, G
    JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) : 1251 - 1255
  • [4] Synthesis of phosphorofluoridate analogues of myo-inositol 1,4,5-tris(phosphate) and their biological activity
    Watanabe, Y
    Sofue, S
    Ozaki, S
    Hirata, M
    CHEMICAL COMMUNICATIONS, 1996, (15) : 1815 - 1816
  • [5] Synthesis and binding properties of cyclopentane analogues of myo-inositol 1,4,5-tris(phosphate)
    Moris, MA
    Caron, AZ
    Guillemette, G
    Schlewer, G
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) : 3995 - 4001
  • [6] D-myo-inositol 1-phosphate as a surrogate of D-myo-inositol 1,4,5-tris phosphate to monitor G protein-coupled receptor activation
    Trinquet, Eric
    Fink, Michel
    Bazin, Herve
    Grillet, Florence
    Maurin, Fabrice
    Bourrier, Emmanuel
    Ansanay, Herve
    Leroy, Cedric
    Michaud, Audrey
    Durroux, Thierry
    Maurel, Damien
    Malhaire, Fanny
    Goudet, Cyril
    Pin, Jean-Philippe
    Naval, Magali
    Hernout, Olivier
    Chretien, Francoise
    Chapleur, Yves
    Mathis, Gerard
    ANALYTICAL BIOCHEMISTRY, 2006, 358 (01) : 126 - 135
  • [7] SYNTHESIS OF 1D-DISTEAROYLPHOSPHATIDYL-MYO-INOSITOL 3,4,5-TRIS(DIHYDROGEN PHOSPHATE)
    WATANABE, Y
    TOMIOKA, M
    OZAKI, S
    TETRAHEDRON, 1995, 51 (33) : 8969 - 8976
  • [8] A CHEMOENZYMATIC SYNTHESIS OF D-MYO-INOSITOL-1,4,5-TRISPHOSPHATE
    LING, L
    OZAKI, S
    CARBOHYDRATE RESEARCH, 1994, 256 (01) : 49 - 58
  • [9] Complexation of spermine and spermidine by myo-inositol 1,4,5-tris(phosphate) and related compounds: Biological significance
    MernissiArifi, K
    Imbs, I
    Schlewer, G
    Spiess, B
    BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 1996, 1289 (03): : 404 - 410
  • [10] A SIMPLE SYNTHESIS OF D-MYO-INOSITOL 4-PHOSPHATE AND D-MYO-INOSITOL 6-PHOSPHATE
    IACOBUCCI, S
    DALARCAO, M
    SYNTHETIC COMMUNICATIONS, 1994, 24 (06) : 809 - 817