title: Solid-supported synthesis of putative peptide beta-turn mimetics via Ugi reaction for diketopiperazine formation.
abstract: The scope and limitations of the solid-supported synthesis of a bicyclic diketopiperazine, an internal, putative peptide beta-turn mimetic, are presented. The 4CC multicomponent Ugi reaction of alpha-N-Boc-diaminopropionic acid resin ester (an amine input), optically active alpha-bromoacid, aldehyde, and isocyanide is the key step in the proposed synthetic protocol. Application of cyclitive cleavage as the final step led to desired products in high purity.
authors.affiliation: Combinatorial Chemistry Group, Health Care Research Center, Procter & Gamble Pharmaceuticals, 8700 Mason-Montgomery Road, P.O. Box 8006, Mason, Ohio 45040-8006, USA. golebiowski.a@pg.com
authors.forename: Adam
authors.initials: A
authors.lastname: Golebiowski
authors.forename: Julita
authors.initials: J
authors.lastname: Jozwik
authors.forename: Sean R
authors.initials: SR
authors.lastname: Klopfenstein
authors.forename: Anny-Odile
authors.initials: AO
authors.lastname: Colson
authors.forename: Arthur L
authors.initials: AL
authors.lastname: Grieb
authors.forename: Anne F
authors.initials: AF
authors.lastname: Russell
authors.forename: Vinit L
authors.initials: VL
authors.lastname: Rastogi
authors.forename: Conrad F
authors.initials: CF
authors.lastname: Diven
authors.forename: David E
authors.initials: DE
authors.lastname: Portlock
authors.forename: Jack J
authors.initials: JJ
authors.lastname: Chen
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D007659:Ketones / Q000138:chemical synthesis*; D008958:Models, Molecular; D018716:Molecular Mimicry; D019151:Peptide Library; D010879:Piperazines / Q000138:chemical synthesis*; D017433:Protein Structure, Secondary; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D019151:Peptide Library; D010879:Piperazines