Next Article in Journal
Analysis of Homogel Uniaxial Compression Strength on Bio Grouting Material
Next Article in Special Issue
Antimicrobial Nanomaterials Derived from Natural Products—A Review
Previous Article in Journal
Enhanced Photocatalytic Activity of CdS-Decorated TiO2/Carbon Core-Shell Microspheres Derived from Microcrystalline Cellulose
Previous Article in Special Issue
A Novel HA/β-TCP-Collagen Composite Enhanced New Bone Formation for Dental Extraction Socket Preservation in Beagle Dogs
Article Menu
Issue 4 (April) cover image

Export Article

Open AccessArticle
Materials 2016, 9(4), 242; doi:10.3390/ma9040242

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
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)
View Full-Text   |   Download PDF [3737 KB, uploaded 29 March 2016]   |  

Abstract

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
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Materials EISSN 1996-1944 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top