Synthesis of constrained analogues of cholecystokinin/opioid chimeric peptides

John M. Ndungu, James P. Cain, Peg Davis, Shou W. Ma, Todd W. Vanderah, Josephine Lai, Frank Porreca, Victor J. Hruby

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

In our ongoing research on the synthesis of constrained analogues of CCK/opioid chimeric peptides, a bicyclic dipeptide mimetic for Nle-Asp was designed and synthesized. Starting from β-allyl substituted aspartic acids, the terminal double bond was oxidized resulting in spontaneous cyclization to form racemic hemiaminals. Allylation of the hemiaminals afforded 5-allyl substituted proline analogues, which on oxidation, Horner-Emmons olefination, asymmetric hydrogenation, and bicyclization afforded bicyclic dipeptide mimetics for Nle-Asp. Constrained CCK/opioid peptide analogues containing bicyclic dipeptide mimetics for Nle-Gly, Nle-Asp, and homoPhe-Gly were then synthesized and analyzed at both the CCK and opioid receptors.

Original languageEnglish (US)
Pages (from-to)2233-2236
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number13
DOIs
StatePublished - Mar 27 2006

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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