β-alanine-based dendritic β-peptides: Dendrimers possessing unusually strong binding ability towards protic solvents and their self-assembly into nanoscale aggregates through hydrogen-bond interactions

Kwok-Kong Mong, Aizhen Niu, Hak Fun Chow*, Chi Wu, Liang Li, Rui Chen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

Abstract

A series of poly(β-alanine) dendrimers 1-4 with Boc-carbamate as the surface functionality, β-alanine as the dendritic branch, 3,5-diaminobenzoic acid as the branching agent, and 1,2-diaminoethane as the interior core has been synthesized by a solution-phase peptide-coupling method. The structural identities and purities of the products have been fully characterized by spectroscopic and chromatographic methods. 1H NMR studies on the dendrimers indicated that the Boc-carbamate surface groups exist as a mixture of syn and anti rotamers in solution, and that the dendrimers adopt an open structure in polar solvents; this allows the free interaction of the interior core functionality with solvent molecules. Due to the cooperative effect of a large number of carbamate and amide groups, the dendrimers exhibit an unusually strong binding ability towards protic solvents and behave as H-bond sponges. As a result, the H/D exchange rates of the N-H protons are significantly enhanced in such dendritic structures, as compared to those of nondendritic carbamates and amides. These dendritic peptide dendrimers also exhibit a strong tendency to form nanoscopic aggregates in nonpolar or polar aprotic solvents through intermolecular H-bond interactions.

Original languageEnglish
Pages (from-to)686-699
Number of pages14
JournalChemistry - A European Journal
Volume7
Issue number3
DOIs
StatePublished - Feb 2001

Keywords

  • Aggregation
  • Amides
  • Dendrimers
  • Peptides

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