Diphosphoinositol Polyphosphates: Polar Stars in Cell Signaling

Abstract

The propagation of information inside cells is achieved in nature by small diffusible molecules. Many of these secondary messengers are highly charged species derived from myo-inositol. The diphosphoinositol polyphosphates (X-PP-myo-InsP₅) represent a novel group of secondary messengers that regulate various important biological processes. Depending on the phosphorylation pattern, these molecules can occur in symmetric or nonsymmetric forms. In a recent study, we have shown the potential of C₂ symmetric phosphoramidites as reagents for desymmetrizing myo-inositol and for obtaining all four possible nonsymmetric X-PP-myo-InsP₅ stereoisomers in enantiomerically pure form. These results and their potential implications for the design of tools for chemical biology are discussed.

Key words

asymmetric synthesis - chiral auxiliaries - phosphorylations - phosphates - protecting groups

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