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.

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 5; no. 11; pp. 1847 - 1850
Main Authors Harris, Paul W. R, Brimble, Margaret A, Gluckman, Peter D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.05.2003
Amer Chemical Soc
Subjects
Bridged Bicyclo Compounds - chemical synthesis
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Conformation
Peptides, Cyclic - chemical synthesis
Physical Sciences
Proline - chemical synthesis
Science & Technology
Stereoisomerism
CARBENE
DIENES
MIMICS
AMINO-ACIDS
OLEFIN METATHESIS
RESIDUE
STEREOSELECTIVE-SYNTHESIS
CONFORMATION
TRIPEPTIDE
DERIVATIVES
Online AccessGet full text

Cover

More Information
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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034370e