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

Organic Letters, ISSN: 1523-7060, Vol: 6, Issue: 19, Page: 3285-3288
2004
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Article Description

(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 -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.

Bibliographic Details

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

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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