SYNTHESIS OF (+/-)-CYCLOHEXANE-1(R),2(R),4(R)-TRIOL-TRIPHOSPHATE, A DEOXYGENATED ANALOG OF MYO-INOSITOL-1,4,5-TRIPHOSPHATE

被引:10
|
作者
SCHMITT, L [1 ]
SPIESS, B [1 ]
SCHLEWER, G [1 ]
机构
[1] CNRS, CTR NEUROCHIM, PHARMACOCHIM MOLEC LAB, 5 RUE BLAISE PASCAL, F-67084 STRASBOURG, FRANCE
关键词
D O I
10.1016/0040-4039(92)88127-Q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
For the use in the studies of inositol-phosphates, (+/-) cyclohexane-1(R), 2(R), 4(R)-triol-triphosphate 2 was synthesized from anisole. The synthesis used 1,2-benzenedimethanol as a ketone and phosphate protective group which induced easy cristallization of the intermediates. Regeneration of the free ketone 9 under mild conditions followed by its selective reduction and phosphorylation by the phosphite method gave the expected compound 2.
引用
收藏
页码:2013 / 2016
页数:4
相关论文
共 50 条
  • [21] Regulation of the inositol 1,4,5-triphosphate receptor by arachidonic acid and eicosanoids.
    Striggow, F
    Ehrlich, BE
    BIOPHYSICAL JOURNAL, 1997, 72 (02) : TU119 - TU119
  • [22] Differential distribution of inositol 1,4,5-triphosphate receptors in the rat olfactory bulb
    Slawecki, ML
    Carlson, GC
    Keller, A
    JOURNAL OF COMPARATIVE NEUROLOGY, 1997, 389 (02) : 224 - 234
  • [23] IMPAIRED D-MYO-INOSITOL 1,4,5-TRIPHOSPHATE GENERATION FROM CORD-BLOOD POLYMORPHONUCLEAR LEUKOCYTES
    SANTORO, P
    AGOSTI, V
    VIGGIANO, D
    PALUMBO, A
    SARNO, T
    CICCIMARRA, F
    PEDIATRIC RESEARCH, 1995, 38 (04) : 564 - 567
  • [24] Role of Inositol 1,4,5-Triphosphate Receptor 2 in Post-Ischemic Heart Failure
    Santulli, Gaetano
    Chen, BiXing
    Forrester, Frances
    Wu, Henry
    Reiken, Steve
    Marks, Andrew R.
    CIRCULATION, 2014, 130
  • [25] Identification of Antibodies Against Inositol 1,4,5-Triphosphate Receptor 1 (IR3R1) in Cerebellar Ataxia and Primary Progressive Multiple Sclerosis
    Alexopolous, Harry
    Fouka, Peneiope
    Chatz, Ioanna
    Dedos, Skariatos
    Samiotaki, Martina
    Panayotou, George
    Politis, Panagiotis
    Tzioufas, Athanasios
    Dalakas, Marinos
    NEUROLOGY, 2016, 86
  • [26] Effects of Inositol 1,4,5-triphosphate on Osteoclast Differentiation in RANKL-induced Osteoclastogenesis
    Son, Aran
    Kim, Min Seuk
    Jo, Hae
    Byun, Hae Mi
    Shin, Dong Min
    KOREAN JOURNAL OF PHYSIOLOGY & PHARMACOLOGY, 2012, 16 (01): : 31 - 36
  • [27] ELECTROPORATION OF INOSITOL 1,4,5-TRIPHOSPHATE INDUCES REPETITIVE CALCIUM OSCILLATIONS IN MURINE OOCYTES
    RICKORDS, LF
    WHITE, KL
    JOURNAL OF EXPERIMENTAL ZOOLOGY, 1993, 265 (02): : 178 - 184
  • [28] PARATHYROID-HORMONE STIMULATES THE GENERATION OF INOSITOL 1,4,5-TRIPHOSPHATE IN BRAIN SYNAPTOSOMES
    SMOGORZEWSKI, M
    ISLAM, A
    AMERICAN JOURNAL OF KIDNEY DISEASES, 1995, 26 (05) : 814 - 817
  • [29] CHARACTERIZATION OF INOSITOL 1,4,5-TRIPHOSPHATE BINDING TO CANINE CARDIAC SARCOPLASMIC-RETICULUM
    KIJIMA, Y
    FLEISCHER, S
    FASEB JOURNAL, 1992, 6 (01): : A423 - A423
  • [30] Inositol 1,4,5-Triphosphate Receptor-binding Protein Released with Inositol 1,4,5-Triphosphate (IRBIT) Associates with Components of the mRNA 3′ Processing Machinery in a Phosphorylation-dependent Manner and Inhibits Polyadenylation
    Kiefer, Helene
    Mizutani, Akihiro
    Iemura, Shun-Ichiro
    Natsume, Tohru
    Ando, Hideaki
    Kuroda, Yukiko
    Mikoshiba, Katsuhiko
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2009, 284 (16) : 10694 - 10705