title: Post-polymerization modification of poly(L-glutamic acid) with D-(+)-glucosamine.
abstract: 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.
authors.affiliation: National Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.
authors.forename: Peter
authors.initials: P
authors.lastname: Perdih
authors.affiliation: National Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.
authors.forename: Sašo
authors.initials: S
authors.lastname: Cebašek
authors.affiliation: National Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.
authors.forename: Alenka
authors.initials: A
authors.lastname: Možir
authors.affiliation: National Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, Slovenia. ema.zagar@ki.si.
authors.forename: Ema
authors.initials: E
authors.lastname: Zagar
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002850:Chromatography, Gel; D017666:Deuterium Oxide / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry*; D008027:Light; D011099:Polyglutamic Acid / Q000737:chemistry*; D058105:Polymerization; D066244:Proton Magnetic Resonance Spectroscopy; D012542:Scattering, Radiation; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D011099:Polyglutamic Acid; D017666:Deuterium Oxide; D005944:Glucosamine