Three-Component Condensation Leading to β-Amino Acid Diamides: Convergent Assembly of β-Peptide Analogues
- 1 October 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (42) , 13606-13607
- https://doi.org/10.1021/ja0450152
Abstract
A Passerini condensation of acyl cyanides, carboxylic acids, and isonitriles has been developed that affords efficient access to functionalized diamides as well as β-peptides of α-hydroxy-β-amino acids. Such compounds are protease-resistant and form stable helical and sheet structures when incorporated into larger peptides. N-Protected α-amino acids and isocyanoesters derived from α-amino acids participate in the condensation, leading to α/β peptides embodying the heterogeneous α/β/α backbone motif, recent examples of which display antibiotic activity.Keywords
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