Solution- and Solid-Phase Synthesis of Triazole Oligomers That Display Protein-Like Functionality
- 20 September 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (21), 7963-7967
- https://doi.org/10.1021/jo701292h
Abstract
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.Keywords
This publication has 18 references indexed in Scilit:
- Microwave Assisted “Click” Chemistry for the Synthesis of Multiple Labeled-Carbohydrate Oligonucleotides on Solid SupportThe Journal of Organic Chemistry, 2006
- Nonpeptidic Foldamers from Amino Acids: Synthesis and Characterization of 1,3-Substituted Triazole OligomersJournal of the American Chemical Society, 2005
- N,N‘-Linked Oligoureas as Foldamers: Chain Length Requirements for Helix Formation in Protic Solvent Investigated by Circular Dichroism, NMR Spectroscopy, and Molecular DynamicsJournal of the American Chemical Society, 2005
- A Microwave-Assisted Click Chemistry Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via a Copper(I)-Catalyzed Three-Component ReactionOrganic Letters, 2004
- The Chemistry of Amine−Azide Interconversion: Catalytic Diazotransfer and Regioselective Azide ReductionJournal of the American Chemical Society, 2002
- A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal AlkynesAngewandte Chemie-International Edition, 2002
- Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to AzidesThe Journal of Organic Chemistry, 2002
- Foldamers: A ManifestoAccounts of Chemical Research, 1998
- Metal catalyzed diazo transfer for the synthesis of azides from aminesTetrahedron Letters, 1996
- Electrophilic activation of the Horner-Wadsworth-Emmons-Wittig reaction: highly selective synthesis of dissymmetric olefinsJournal of the American Chemical Society, 1992