Three-component condensation leading to beta-amino acid diamides: convergent assembly of beta-peptide analogues.
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.
Oaksmith
Jennifer M
JM
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Peters
Ulf
U
Ganem
Bruce
B
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary
D000577:Amides; D000596:Amino Acids; D010455:Peptides