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Supramolecular structure and anomer‐selective formation of polyglucuronic acid
Author(s) -
Stetco I. Alina,
Merschrod S Erika F
Publication year - 2013
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.4367
Subject(s) - glycosidic bond , chemistry , anomer , supramolecular chemistry , nmr spectra database , selectivity , cellulose , carbon 13 nmr , stereochemistry , crystallography , polymer chemistry , organic chemistry , molecule , catalysis , spectral line , physics , astronomy , enzyme
Polyglucuronic acids provide a biocompatible matrix for industries ranging from pharmaceuticals to agriculture. Here we provide a method for selectively producing α‐polyglucuronic acid, a simple alternative to the oxidation of cellulose or amylose with 2,2,6,6‐tetramethylpiperidine‐1‐oxyl radical ( TEMPO ) or isolation from bacterial cultures. Atomic force micrographs show the pH ‐dependent formation and persistence of polyglucuronic acid fibrils, while NMR studies demonstrate the selectivity of the glycosidic linkage. By controlling pH , oligoglucuronate chains are created, with both NMR and AFM data showing the preservation of this linkage in basic medium after formation under acid. Clear evidence for the formation of the C–O–C glycosidic bond comes from peaks in the 13 C NMR spectra, revealing a linkage through the anomeric carbon atom and also a linkage with a ring carbon atom.