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

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

Peter Perdih, Andrej Kržan, Ema Žagar

Materials (Basel). 2016 Mar 29;9(4):242.

PMID: 28773369

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS76240	Polyester-8-hydroxyl-1-acetylene bis-MPA dendron, generation 3			Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: