Synthesis of Diverse Macrocyclic Peptidomimetics Utilizing Ring-Closing Metathesis and Solid-Phase Synthesis

The synthesis of a range of highly functionalized peptidomimetic macrocycles has been accomplished using ring-closing metathesis and enyne tandem cross-metathesis−ring-closing metathesis reactions. This approach gives access to rigidified macrocycles modeled on the structures of cyclic peptides and...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-02, Vol.69 (4), p.1028-1037
Main Authors: Barrett, Anthony G. M, Hennessy, Alan J, Vézouët, Ronan Le, Procopiou, Panayiotis A, Seale, Peter W, Stefaniak, Stefan, Upton, Richard J, White, Andrew J. P, Williams, David J
Format: Article
Language:English
Subjects:
Alkylation
Chemistry
Crystallography, X-Ray
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Molecular Structure
Organic chemistry
Peptides
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Preparations and properties
Stereoisomerism
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Summary:The synthesis of a range of highly functionalized peptidomimetic macrocycles has been accomplished using ring-closing metathesis and enyne tandem cross-metathesis−ring-closing metathesis reactions. This approach gives access to rigidified macrocycles modeled on the structures of cyclic peptides and designed to be biologically stable. The potential for peripheral functionalization of these templates has been demonstrated using Diels−Alder reactions, palladium(0) coupling reactions, and amide formation both in the solution phase and using polymer-supported syntheses.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0352629