Synthesis of Cyclic Proline-Containing Peptides via Ring-Closing Metathesis

Several dienes embedded in di- and tripeptides which incorporate proline have been prepared and subjected to ring-closing metathesis. Bicyclic peptides of well-defined amide geometry and of varying ring sizes were prepared. Several limitations of the cyclization step were revealed.

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Bibliographic Details
Published in:Organic letters 2003-05, Vol.5 (11), p.1847-1850
Main Authors: Harris, Paul W. R, Brimble, Margaret A, Gluckman, Peter D
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds - chemical synthesis
Catalysis
Cyclization
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Conformation
Peptides, Cyclic - chemical synthesis
Proline - chemical synthesis
Stereoisomerism
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Description
Summary:Several dienes embedded in di- and tripeptides which incorporate proline have been prepared and subjected to ring-closing metathesis. Bicyclic peptides of well-defined amide geometry and of varying ring sizes were prepared. Several limitations of the cyclization step were revealed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034370e