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Synthesis of Dendronized Poly(l-Glutamate) via Azide-Alkyne Click Chemistry

Laboratory for Polymer Chemistry and Technology, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia
Author to whom correspondence should be addressed.
Academic Editors: Marek M. Kowalczuk and Guozhan Jiang
Materials 2016, 9(4), 242;
Received: 29 February 2016 / Revised: 17 March 2016 / Accepted: 23 March 2016 / Published: 29 March 2016
(This article belongs to the Special Issue Biodegradable and Bio-Based Polymers)
Poly(l-glutamate) (PGlu) was modified with a second-generation dendron to obtain the dendronized polyglutamate, P(Glu-D). Synthesized P(Glu-D) exhibited a degree of polymerization (DPn) of 46 and a 43% degree of dendronization. Perfect agreement was found between the P(Glu-D) expected structure and the results of nuclear magnetic resonance spectroscopy (NMR) and size-exclusion chromatography coupled to a multi-angle light-scattering detector (SEC-MALS) analysis. The PGlu precursor was modified by coupling with a bifunctional building block (N3-Pr-NH2) in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) coupling reagent. The second-generation polyamide dendron was prepared by a stepwise procedure involving the coupling of propargylamine to the l-lysine carboxyl group, followed by attaching the protected 2,2-bis(methylol)propionic acid (bis-MPA) building block to the l-lysine amino groups. The hydroxyl groups of the resulting second-generation dendron were quantitatively deprotected under mild acidic conditions. The deprotected dendron with an acetylene focal group was coupled to the pendant azide groups of the modified linear copolypeptide, P(Glu-N3), in a Cu(I) catalyzed azide-alkyne cycloaddition reaction to form a 1,4-disubstituted triazole. The dendronization reaction proceeded quantitatively in 48 hours in aqueous medium as confirmed by 1H NMR and Fourier transform infrared spectroscopy (FT-IR) spectroscopy. View Full-Text
Keywords: dendronized polymer; poly(l-glutamate); bis-MPA; l-lysine; “click” reaction dendronized polymer; poly(l-glutamate); bis-MPA; l-lysine; “click” reaction
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MDPI and ACS Style

Perdih, P.; Kržan, A.; Žagar, E. Synthesis of Dendronized Poly(l-Glutamate) via Azide-Alkyne Click Chemistry. Materials 2016, 9, 242.

AMA Style

Perdih P, Kržan A, Žagar E. Synthesis of Dendronized Poly(l-Glutamate) via Azide-Alkyne Click Chemistry. Materials. 2016; 9(4):242.

Chicago/Turabian Style

Perdih, Peter, Andrej Kržan, and Ema Žagar. 2016. "Synthesis of Dendronized Poly(l-Glutamate) via Azide-Alkyne Click Chemistry" Materials 9, no. 4: 242.

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