Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine
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 hy...
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doaj-72cab61ddeb741ec92fc4b81556b47082020-11-24T20:47:03ZengMDPI AGMolecules1420-30492014-11-011912197511976810.3390/molecules191219751molecules191219751Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-GlucosaminePeter Perdih0Sašo Čebašek1Alenka Možir2Ema Žagar3National Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, SloveniaNational Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, SloveniaNational Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, SloveniaNational Institute of Chemistry, Laboratory for Polymer Chemistry and Technology, Hajdrihova 19, SI-1000 Ljubljana, SloveniaCarboxyl 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.http://www.mdpi.com/1420-3049/19/12/19751poly(L-glutamic acid)glucosamineglycopolypeptide |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Peter Perdih Sašo Čebašek Alenka Možir Ema Žagar |
spellingShingle |
Peter Perdih Sašo Čebašek Alenka Možir Ema Žagar Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine Molecules poly(L-glutamic acid) glucosamine glycopolypeptide |
author_facet |
Peter Perdih Sašo Čebašek Alenka Možir Ema Žagar |
author_sort |
Peter Perdih |
title |
Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine |
title_short |
Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine |
title_full |
Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine |
title_fullStr |
Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine |
title_full_unstemmed |
Post-Polymerization Modification of Poly(L-glutamic acid) with D-(+)-Glucosamine |
title_sort |
post-polymerization modification of poly(l-glutamic acid) with d-(+)-glucosamine |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2014-11-01 |
description |
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. |
topic |
poly(L-glutamic acid) glucosamine glycopolypeptide |
url |
http://www.mdpi.com/1420-3049/19/12/19751 |
work_keys_str_mv |
AT peterperdih postpolymerizationmodificationofpolylglutamicacidwithdglucosamine AT sasocebasek postpolymerizationmodificationofpolylglutamicacidwithdglucosamine AT alenkamozir postpolymerizationmodificationofpolylglutamicacidwithdglucosamine AT emazagar postpolymerizationmodificationofpolylglutamicacidwithdglucosamine |
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