Novel design of bicyclic β-turn dipeptides on solid-phase supports and synthesis of [3.3.0]-bicyclo[2,3]-leu-enkephalin analogues

Xuyuan Gu, Jinfa Ying, Richard S. Agnes, Edita Navratilova, Peg Davis, Gannon Stahl, Frank Porreca, Henry I. Yamamura, Victor J. Hruby

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

(Chemical Equation Presented) External bicyclic β-turn dipeptide mimetics provide an excellent design approach that can offer a rich chiral ensemble of structures with different backbone conformations. We report herein a novel design of a convergent combinatorial synthetic methodology, which is illustrated by the solid-phase synthesis of a series of [3.3.0]-bicyclo [2,3]-Leu-enkephalin analogues. The reactions were optimized and the epimeric configurations were determined by 2D NMR spectroscopy. Biological assays show that these analogues have more potent δ binding affinity and bioactivity for δ vs μ opioid receptor, which may be related to the different conformations preferred by these analogues in our modeling studies.

Original languageEnglish (US)
Pages (from-to)3285-3288
Number of pages4
JournalOrganic Letters
Volume6
Issue number19
DOIs
StatePublished - Sep 16 2004

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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