Modular synthesis of cyclic peptidomimetics inspired by gamma-turns.
[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.
Ramanathan
Senthil Kumar
SK
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Keeler
John
J
Lee
Huey-Lih
HL
Reddy
D Srinavasa
DS
Lushington
Gerald
G
Aubé
Jeffrey
J
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
D000596:Amino Acids; D001381:Azepines; D001386:Azides; D007202:Indicators and Reagents; D010456:Peptides, Cyclic