Inframolecular acid–base and coordination properties towards Na⁺and Mg²⁺of myo-inositol 1,3,4,5,6-pentakisphosphate: a structural approach to biologically relevant species

Abstract

We present the chemical and structural study of the inframolecular aspects of Ins(1,3,4,5,6)P 5 protonation and complexation equilibria with biological cations.

Interaction of myo-inositol hexakisphosphate with biogenic and synthetic polyamines

“…In this sense, we have studied so far, under simulated physiological conditions, the complex chemical reactivity displayed by the most important InsPs, with special attention to metal cation interactions. [15][16][17][18][19][20][21][22][23] We have also recently reported the first crystallographic evidence of the interaction of Cu(II) with an InsP in a mixed-ligand complex. 24 The hexaphosphorylated InsP, InsP 6 (L 12− in its fully deprotonated form, Fig.…”

“…They participate in a number of complex intertwined chemical processes that have complicated the biochemical and biological research on the cellular roles of InsPs. [15][16][17][18][19][20][21][22][23] We have also recently reported the first crystallographic evidence of the interaction of Cu(II) with an InsP in a mixed-ligand complex. [9][10][11][12][13][14] Stoichiometry, charge, solubility, relative stability and structural features of the biologically relevant InsPs species influence their biological func-tions at the cellular level.…”

The “Other” Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances inmyo‐Inositol Chemistry)

“…[210] Ins(1,3,4,5,6)P 5 (157) and related derivatives were recently synthesized using a route from the myo-inositol 1,3,5-orthobenzoate leading regioselectively to the precursor 2-O-benzoylmyo-inositol (158) via a 1,2-bridged 2′-phenyl-1′,3′-dioxolan-2′-ylium ion. [211] Substituted pentakisphosphate derivatives are of interest and 2-O-benzyl-myo-inositol 1,3,4,5,6-pentakisphosphate, 2-O-Bn-Ins(1,3,4,5,6)P 5 (159), showed anticancer activity in xenograft studies and also is a nanomolar inhibitor of 3-phosphoinositide-dependent protein kinase 1 (PDK1).…”

“…The butane diacetal (BDA) groups were then removed under acidic conditions and phosphitylation of the hydroxyl groups with reagent 173, then oxidation of the products gave the fully blocked compound 209. All benzyl groups were removed in one step to give the target compound, 5-PA-InsP 5 (210), in excellent yield. Diol 188 was a key starting intermediate for the synthesis of two further analogues.…”

“…The higher phosphorylated myo ‐inositol derivatives include isomers of myo ‐inositol pentakisphosphate, for example, myo ‐inositol 1,3,4,5,6‐pentakisphosphate ( 157 ), the metal ion coordination properties of which have recently been explored . Ins(1,3,4,5,6)P 5 ( 157 ) and related derivatives were recently synthesized by using a route from myo ‐inositol 1,3,5‐orthobenzoate that led regioselectively to the precursor 2‐ O ‐benzoyl‐ myo ‐inositol ( 158 ) via a 1,2‐bridged 2′‐phenyl‐1′,3′‐dioxolan‐2′‐ylium ion .…”