Solid-supported synthesis of a peptide beta-turn mimetic.
[structure: see text]The solid-supported synthesis of a bicyclic diketopiperazine, a potential peptide beta-turn mimetic, is described. The Ugi reaction between the resin ester of alpha-N-Boc-diaminopropionic acid (an amine input), alpha-bromo acid, aldehyde, and isocyanide is the key step in the proposed protocol.
Golebiowski
A
A
Procter & Gamble Pharmaceuticals, Combinatorial Chemistry Group, Health Care Research Center, Mason, Ohio 45040-8006, USA. golebiowskia@pg.com
Klopfenstein
S R
SR
Shao
X
X
Chen
J J
JJ
Colson
A O
AO
Grieb
A L
AL
Russell
A F
AF
D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D008958:Models, Molecular; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010879:Piperazines / Q000737:chemistry; D017433:Protein Structure, Secondary; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D015091:beta-Alanine / Q000031:analogs & derivatives / Q000737:chemistry
D007202:Indicators and Reagents; D010455:Peptides; D010879:Piperazines; D015091:beta-Alanine; C011757:2,3-diaminopropionic acid