title: Modular synthesis of cyclic peptidomimetics inspired by gamma-turns.
abstract: [reaction: see text] A series of peptidomimetics based on a gamma-turn motif were synthesized using a modular approach, in which N-protected piperidones were reacted with a selection of 2-hydroxyalkyl azides derived from common l-amino acids. Hydrolysis of the initially formed iminium ethers afforded the targeted series of substituted 1,4-diazepin-5-ones.
authors.affiliation: Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, University of Kansas, Lawrence, Kansas 66045-7582, USA.
authors.forename: Senthil Kumar
authors.initials: SK
authors.lastname: Ramanathan
authors.forename: John
authors.initials: J
authors.lastname: Keeler
authors.forename: Huey-Lih
authors.initials: HL
authors.lastname: Lee
authors.forename: D Srinavasa
authors.initials: DS
authors.lastname: Reddy
authors.forename: Gerald
authors.initials: G
authors.lastname: Lushington
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D007202:Indicators and Reagents; D018716:Molecular Mimicry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001381:Azepines; D001386:Azides; D007202:Indicators and Reagents; D010456:Peptides, Cyclic