Interaction of phytate with cyclic polyamines

myo -Inositol hexakisphosphate (InsP 6 ) is a widespread molecule, present in relatively high concentrations in nature, and plays key roles in many metabolic processes. Its complex chemistry arises from the presence of flexible ring bearing six multivalent phosphates that can either be anionic or in...

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Bibliographic Details
Published in:New journal of chemistry 2023-12, Vol.48 (1), p.39-321
Main Authors: Torres, Julia, Veiga, Nicolás, Savastano, Matteo, Kremer, Carlos, Bianchi, Antonio
Format: Article
Language:English
Subjects:
Biomolecules
Cations
Charge distribution
Electrical measurement
Hexamine
Hydrogen bonding
Inositols
Phosphates
Polyamines
Potentiometric analysis
Software
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Summary:myo -Inositol hexakisphosphate (InsP 6 ) is a widespread molecule, present in relatively high concentrations in nature, and plays key roles in many metabolic processes. Its complex chemistry arises from the presence of flexible ring bearing six multivalent phosphates that can either be anionic or interact with a myriad of cationic species in solution, including protonated polyamines. Understanding the interaction of this biomolecule with inorganic and organic cations aims to gain a better picture of its chemical and structural behavior in biological systems. Building on our previous work on the interaction of InsP 6 with inorganic cations and linear polyamines, here, in this study, we present the corresponding interaction with cyclic polyamines via potentiometry, with the help of computational tools, in order to understand the main determinants of the stability of the formed species and the structural insights that rationalize the interaction. Stable InsP 6  : polyamine 1 : 1 species are detected and the strength of the interaction results from an interplay of electrostatic attractions and hydrogen bonding formation. Even though the results show a certain resemblance to the interaction of InsP 6 with linear polyamines, the higher rigidity imposed by cyclization increases the selectivity of InsP 6 towards polyamines, giving rise to the molecular recognition of hexamine 18N6, due to the spatial geometric fit of the charge distribution of the interacting anionic InsP 6 and the protonated polyamine. Potentiometric and computational studies demonstrated the strong interaction based on electrostatic attraction and modulated by H-bond contact formation and dimensional fit. Cyclization leads to a marked selectivity of phytate towards hexamine.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj04652d