1996•Tetrahedron LettersOpen access

Synthesis of novel metabolically stable analogues of D-myo-inositol 1,4,5-trisphosphate

Abdul H. Fauq, Javid H. Zaidi, Robert A. Wilcox, Girlie Varvel, Stefan R. Nahorski, Alan P. Kozikowski, Christophé Erneux

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Abstract

Starting from L-quebrachitol, syntheses and biological activities of three novel analogues of the cellular second messenger D-myo-inositol 1,4,5-trisphosphate (IP3), 3-deoxy-3-fluoro-d-myo-inositol 1,4-bisphosphate 5-phosphorothioate (1a), 3-deoxy-3-fluoro-d-myo-inositol 1,5-bisphosphate 4-phosphorothioate (1b), and 3-deoxy-3-fluoro-d-myo-inositol 1-phosphate 4,5-bisphosphorothioate (1c) are described.

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Key concepts: Inositol, Chemistry, Cyclitol, Inositol phosphate, Second messenger system, Stereochemistry, Inositol trisphosphate, Biochemistry