Phosphorylation of Hyaluronic Acid

Chemical phosphorylation of hyaluronic acid (HA) remains an unresolved problem for the chemistry of this unique polysaccharide, since convenient phosphorylating reagents are not reactive enough to obtain HA phosphates (HA-P) with a satisfactory degree of esterification of hydroxyl groups. The synthe...

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Bibliographic Details
Published in:Chemistry Proceedings 2022-11, Vol.12 (1), p.39
Main Authors: Elvira A. Khaybrakhmanova, Stanislav V. Kozyrev, Tatyana V. Tyumkina, Irina Yu. Ponedel’kina
Format: Article
Language:English
Subjects:
dry phosphorylation
hyaluronic acid
oxide phosphorus (V)
polyphosphates
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Summary:Chemical phosphorylation of hyaluronic acid (HA) remains an unresolved problem for the chemistry of this unique polysaccharide, since convenient phosphorylating reagents are not reactive enough to obtain HA phosphates (HA-P) with a satisfactory degree of esterification of hydroxyl groups. The synthesis of phosphates of low-molecular-weight (43 kDa) and high-molecular-weight (0.5–0.7 MDa) HA was undertaken using such reagents as sodium trimetaphosphate Na3P3O9, H3PO4, NaH2PO4/Na2HPO4, and anhydride P2O5. Solid-phase HA esterification with P2O5 was found to be the most convenient and efficient method. The HA-P samples were characterized by XRF and NMR spectroscopy (31P and 1H-31P) and contained, depending on the HA/P2O5 ratio, 0.30–6.25% P wt., in the form of disubstituted mono-, di-, and polyphosphates.
ISSN:2673-4583
DOI:10.3390/ecsoc-26-13535