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

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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Main Authors: Peter Perdih, Sašo Čebašek, Alenka Možir, Ema Žagar
Format: Article
Language:English
Published: MDPI AG 2014-11-01
Series:Molecules
Subjects:
poly(L-glutamic acid)
glucosamine
glycopolypeptide
Online Access:http://www.mdpi.com/1420-3049/19/12/19751
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spelling 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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