title: Three-component condensation leading to beta-amino acid diamides: convergent assembly of beta-peptide analogues.
abstract: A Passerini condensation of acyl cyanides, carboxylic acids, and isonitriles has been developed that affords efficient access to functionalized diamides as well as beta-peptides of alpha-hydroxy-beta-amino acids. Such compounds are protease-resistant and form stable helical and sheet structures when incorporated into larger peptides. N-Protected alpha-amino acids and isocyanoesters derived from alpha-amino acids participate in the condensation, leading to alpha/beta peptides embodying the heterogeneous alpha/beta/alpha backbone motif, recent examples of which display antibiotic activity.
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Oaksmith
authors.forename: Ulf
authors.initials: U
authors.lastname: Peters
authors.forename: Bruce
authors.initials: B
authors.lastname: Ganem
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary
chemical_list: D000577:Amides; D000596:Amino Acids; D010455:Peptides