Organic biomolecules bind to phosphate through borate linkages in aqueous solutions

Abstract

Solutions of salicyclic, ascorbic, and citric acids were reacted with boric acid, followed by NaH 2 PO 4 . The products, triphosphateborate ester of salicylic acid (1), orthosphateborate ester of ascorbic acid (2), triphosphateborate ester of ascorbic acid (3), and orthosphateborate ester of citric acid (4), were flash precipitated with cold acetone and characterised by microanalysis, thermal analysis, FT-IR, Raman, 11 B NMR, 31 P MAS NMR, and mass spectroscopic techniques. Analytical results indicated the presence of -C-O-B-O-P-linkages with the attached phosphate groupsvarying between orthophosphate and triphosphate, depending on the starting material. The biomolecules studied in this work may serve as models in the B-P-organic system and the results would provide a possible contribution to boron prebiotic chemistry.

Boric acid: a simple molecule of physiologic, therapeutic and prebiotic significance

“…Depending on the alterations in composition and temperature, chiral crystalline derivatives of these hydrogels could lead to the enantiometric enrichment of the racemic ribose on surface which then determines the chirality of amino acids. Our recent work [59] provides experimental evidence in favor of this hypothesis. We examined possible formation of -C-O-B-O-P-linkages in aqueous media by adding orthophosphate to solutions of boric acid and some biomolecules (Fig.…”

Bioactive glasses prepared from organic-mediated BOP bonded materials

“…Phosphateborate esters of salicyclic, ascorbic and citric acids were isolated from solutions containing boric acid, NaH 2 PO 4 and the bioacid; details are given elsewhere [26]. Esterification reaction was conducted in two steps: In the first step, borate monoesters were prepared in situ by adding solid H 3 BO 3 into the solutions containing the sodium salt of the respective acid in a 1:1 molar ratio and stirring the solution for 1 h, as described previously [27][28][29].…”

“…Here we introduce an alternative route for the synthesis of borate-phosphate glasses. During our work on the investigation of \C\O\B\O\P\ bond formation in aqueous solutions [26], we noticed that the isolated esterification products between an organic acid (salicylic acid, ascorbic acid, citric acid), boric acid and sodium dihydrogen phosphate glassified on heating. Bubble-free glasses with significant bioactivity were obtained from powder \C\O\B\O\P\ bonded materials via melt-quench technique and characterized by a variety of structural analysis methods.…”