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.
Highlights
Dendronized polymers consist of dendrons attached to a linear polymer backbone [1,2,3,4]
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 building block to the L-lysine amino groups
Summary
Dendronized polymers consist of dendrons attached to a linear polymer backbone [1,2,3,4]. The presence of charged peripheral groups [7,8] to the structure of dendronized polymers was investigated thoroughly by Schlüter’s group. Dendronized polymers possess a large number of peripheral functional groups due to their branched structure. Together with the distinctive size and shape, make the dendronized polymers very interesting for potential application in various fields such as biomedicine [9,10,11,12], recognition of metal cations [13,14,15], biocatalysis [16], bacteria detection [17], and to prepare self-assembled ordered structures [2,18]
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