Application of Microwave Irradiation to the Synthesis of 14-Helical β-Peptides
- 22 March 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (8) , 1517-1520
- https://doi.org/10.1021/ol0501727
Abstract
We have evaluated the effects of microwave irradiation on the solid-phase synthesis of β-peptides. Sequences designed to adopt the 14-helix, especially those containing the structure-promoting residue trans-2-aminocyclohexanecarboxylic acid (ACHC), suffer from poor synthetic efficiency under standard SPPS conditions. A comparison of microwave and conventional heating shows that both provide excellent synthetic results for shorter sequences; however, we identify a clear benefit from microwave irradiation for longer β-peptides.Keywords
This publication has 30 references indexed in Scilit:
- Controlled Microwave Heating in Modern Organic SynthesisAngewandte Chemie International Edition in English, 2004
- Developments in peptide and amide synthesisCurrent Opinion in Chemical Biology, 2004
- Focused™ microwave instrumentation from CEM corporationMolecular Diversity, 2003
- β-Peptides: From Structure to FunctionChemical Reviews, 2001
- Formation of Short, Stable Helices in Aqueous Solution by β-Amino Acid HexamersJournal of the American Chemical Society, 1999
- Foldamers: A ManifestoAccounts of Chemical Research, 1998
- β-Peptides: a surprise at every turnChemical Communications, 1997
- β‐Peptides: Synthesis by Arndt‐Eistert homologation with concomitant peptide coupling. Structure determination by NMR and CD spectroscopy and by X‐ray crystallography. Helical secondary structure of a β‐hexapeptide in solution and its stability towards pepsinHelvetica Chimica Acta, 1996
- β-Peptide Foldamers: Robust Helix Formation in a New Family of β-Amino Acid OligomersJournal of the American Chemical Society, 1996
- Enhanced coupling efficiency in solid-phase peptide synthesis by microwave irradiationThe Journal of Organic Chemistry, 1992