Bioorganic and Medicinal Chemistry p. 1021 - 1034 (1996)
Update date:2022-09-26
Topics:
Smith III, Amos B.
Knight, Steven D.
Sprengeler, Paul A.
Hirschmann, Ralph
The de novo design and initial synthetic studies directed toward construction of a novel non-peptide scaffold for β-strand/sheet and related secondary peptide structural mimics are described. The scaffold, consisting of a repeating array of 2,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains, is conceptually related to our previously successful 3,5-linked polypyrrolinone non-peptide peptidomimetic scaffold. Construction of the 2,5,5-trisubstituted pyrrolinone ring system proceeds via intramolecular condensation of an N-protected amino dione. The latter is prepared from a protected α-amino ketone and aldehyde via an aldol-oxidation reaction sequence.
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