title: Design and Asymmetric Synthesis of beta-Strand Peptidomimetics.
abstract: We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important side chains and backbone elements of the Phe43-Lys46 segment.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139.
authors.forename: Ahcene
authors.initials: A
authors.lastname: Boumendjel
authors.forename: John C.
authors.initials: JC
authors.lastname: Roberts
authors.forename: Essa
authors.initials: E
authors.lastname: Hu
authors.forename: Peter V.
authors.initials: PV
authors.lastname: Pallai
authors.forename: Julius
authors.initials: J
authors.lastname: Rebek