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Open AccessArticle

Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine

National Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, Slovenia
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Molecules 2014, 19(12), 19751-19768; https://doi.org/10.3390/molecules191219751
Received: 30 October 2014 / Revised: 20 November 2014 / Accepted: 24 November 2014 / Published: 27 November 2014
(This article belongs to the Special Issue Ring-Opening Polymerization)
Carboxyl functional groups of poly(L-glutamic acid) (PGlu) were modified with a D-(+)-glucosamine (GlcN) by amidation using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) as a coupling reagent. The coupling reaction was performed in aqueous medium without protection of hydroxyl functional groups of D-(+)-glucosamine. Poly(L-glutamic acid) and GlcN functionalized polyglutamates (P(Glu-GlcN)) were thoroughly characterized by 1D and 2D NMR spectroscopy and SEC-MALS to gain detailed information on their structure, composition and molar mass characteristics. The results reveal successful functionalization with GlcN through the amide bond and also to a minor extent through ester bond formation in position 1 of GlcN. In addition, a ratio between the α- and β-form of glucosamine substituent coupled to polyglutamate repeating units as well as the content of residual dimethoxy triazinyl active ester moiety in the samples were evaluated. View Full-Text
Keywords: poly(L-glutamic acid); glucosamine; glycopolypeptide poly(L-glutamic acid); glucosamine; glycopolypeptide
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Perdih, P.; Čebašek, S.; Možir, A.; Žagar, E. Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine. Molecules 2014, 19, 19751-19768.

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