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Selective monophosphorylation of chitosan via phosphorus oxychloride.


ABSTRACT: Chitosan was selectively monophosphorylated via reaction with phosphorus oxychloride (POCl3) to enhance water solubility while avoiding polyphosphate formation. The use of POCl3 resulted in negligible product degradation (i.e., breakdown of O-glycosidic bonds) even after a 3 d reaction period (<5% weight loss). X-ray photoelectron spectroscopy (XPS) characterization of the POCl3-phosphorylated chitosan (P-chitosan) revealed a phosphorus to nitrogen (P/N) atomic ratio of 0.30. Phosphorus-31 nuclear magnetic resonance (31P NMR) spectroscopy verified the monophosphorylation of chitosan's primary and secondary alcohols, and primary amines. The calcium chelation efficiency for the phosphorylated product approached 0.05 mg Ca2+ per mg of P-chitosan as measured by inductively coupled plasma-optical emission spectrometry (ICP-OES), indicating improved chelation over native chitosan. This selective monophosphorylation approach proved useful for modifying other biopolymers, including cellulose and alginate.

SUBMITTER: Suchyta DJ 

PROVIDER: S-EPMC5646824 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Selective monophosphorylation of chitosan via phosphorus oxychloride.

Suchyta Dakota J DJ   Soto Robert J RJ   Schoenfisch Mark H MH  

Polymer chemistry 20170331 16


Chitosan was selectively monophosphorylated via reaction with phosphorus oxychloride (POCl<sub>3</sub>) to enhance water solubility while avoiding polyphosphate formation. The use of POCl<sub>3</sub> resulted in negligible product degradation (i.e., breakdown of <i>O</i>-glycosidic bonds) even after a 3 d reaction period (<5% weight loss). X-ray photoelectron spectroscopy (XPS) characterization of the POCl<sub>3</sub>-phosphorylated chitosan (P-chitosan) revealed a phosphorus to nitrogen (P/N) a  ...[more]

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