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A study was conducted on the design and total synthesis of DL-6-deoxy-6-(hydroxymethyl)-scyllo-inositol 1:7-cyclic 2,4-triphosphate, a conformationally restricted cyclic phosphate analogue of the second messenger inositol 1,4,5-triphosphate [Ins(1,4,5)P3]. The findings indicate that the complex behaves as a diprotic acid over the physiological pH range and that the ionization of the phosphate group equivalent to the 5-phosphate of Ins(1,4,5)P3 is enhanced.

Two carbohydrate ring contraction reactions were performed to obtain chiral, mimics of D-myo-inositol 1,4,5-triphosphate from D-glucose. The analogs, which activate intracellular Ca(sup 2+) despite the absence of a six-membered ring, were 3-hydroxy-1,2,4-trisphosphono-5-vinylcyclopentane, 3-hydroxy-5-(hydroxymethyl)-1,2,4-trisphosphocyclopentane and 1,2-dihydroxy-3,4-bis(phosphonooxy)-5-((phosphonooxy)methyl)cyclopentane.

The structural similarity between different structurally modified analogs helps in finding the deeper insight of inositol trisphosphate. The adenophostins A and B obtained from Penicillium brevicompactum behave as inositol trisphosphate receptor agonists. The inositol trisphosphate receptor takes part in the Ca ion release and the two phosphate groups interact with the receptor and form an integral ion channel although there is a reduction in charge.

Acid hydrolysis of myo-inositol 1,3,5-orthoesters, apart from orthoformates, exclusively affords the corresponding 2-O-acyl myo-inositol products via a 1,2-bridged five-membered ring dioxolanylium ion intermediate observed by NMR spectroscopy. These C-2-substituted inositol derivatives provide valuable precursors for rapid and highly efficient routes to 2-O-acyl inositol 1,3,4,5,6-pentakisphosphates and myo-inositol 1,3,4,5,6-pentakisphosphate with biologically interesting and anticancer properties. Deuterium incorporation into the α-methylene group of such alkyl ester products (2-O-C(O)CD2R), when the analogous alkyl orthoester is treated with deuterated acid, is established utilizing the novel orthoester myo-inositol 1,3,5-orthobutyrate as an example. Such deuterated ester products provide intermediates for deuterium-labeled synthetic analogues. Investigation into this selective formation of 2-O-ester products and the deuterium incorporation is presented with proposed mechanisms from NMR experiments. [ABSTRACT FROM AUTHOR]