Solution- and solid-phase synthesis of triazole oligomers that display protein-like functionality

Nicholas G. Angelo, Paramjit S. Arora

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) We recently developed a new class of oligomers that contain α-amino acid residues linked by 1,2,3-triazole groups [Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134-17135]. Synthesis of these oligomers involves an iterative sequence consisting of diazotransfer and Huisgen 1,3-dipolar cycloaddition steps. In this contribution, we describe an efficient one-pot, two-step sequence for the preparation of triazoles from the corresponding amino acid-derived amines and alkynes in solution. The one-pot sequence affords the desired products in significantly higher yields than our original method. We also outline a highly effective protocol for the synthesis of these triazole-based biomimetic oligomers on the solid phase. We find that amino acid derivatives and iterative formation of triazole rings require nontraditional reaction conditions for high yields.

Original languageEnglish (US)
Pages (from-to)7963-7967
Number of pages5
JournalJournal of Organic Chemistry
Volume72
Issue number21
DOIs
StatePublished - Oct 12 2007

ASJC Scopus subject areas

  • Organic Chemistry

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