Convenient synthesis of 3- and 6-deoxy-D-myo-inositol phosphate analogues from (+)-epi- and (-)-vibo-quercitols.
Starting from (+)-epi- and (-)-vibo-quercitols readily produced by bioconversion of myo-inositol, some biologically interesting phosphate and polyphosphate analogues, including the Ins(1,4,5)P(3) derivatives of 3-deoxy- and 6-deoxy-D-myo-inositol, could be readily prepared in a conventional manner. In addition, chemical modification at C-2 of the 3-deoxy Ins(1,4,5)P(3) provided 2-epimer, and 2-deoxy and 2-deoxy-2-fluoro forms. Eight polyphosphate analogues obtained were assayed for biological activity against PDH-Pase and PDH-K, and G6Pase, but none proved positive.
Ogawa
Seiichiro
S
Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Hiyoshi, Yokohama 223-8522, Japan. sogawa379@ybb.ne.jp
Tezuka
Yoji
Y
D000818:Animals; D005952:Glucose-6-Phosphatase / Q000187:drug effects; D006801:Humans; D007294:Inositol / Q000031:analogs & derivatives / Q000737:chemistry; D007295:Inositol Phosphates / Q000138:chemical synthesis* / Q000494:pharmacology; D011122:Polyphosphates; D011494:Protein Kinases / Q000187:drug effects; D017346:Protein Serine-Threonine Kinases; D011769:Pyruvate Dehydrogenase (Lipoamide)-Phosphatase / Q000187:drug effects; D000081382:Pyruvate Dehydrogenase Acetyl-Transferring Kinase; D013329:Structure-Activity Relationship
D007295:Inositol Phosphates; D011122:Polyphosphates; D000081382:Pyruvate Dehydrogenase Acetyl-Transferring Kinase; C443720:allo-quercitol; D007294:Inositol; D011494:Protein Kinases; D017346:Protein Serine-Threonine Kinases; D011769:Pyruvate Dehydrogenase (Lipoamide)-Phosphatase; D005952:Glucose-6-Phosphatase