Synthesis of cyclic proline-containing peptides via ring-closing metathesis

Paul W R Harris; Margaret A Brimble; Peter D Gluckman

doi:10.1021/ol034370e

Synthesis of cyclic proline-containing peptides via ring-closing metathesis

Org Lett. 2003 May 29;5(11):1847-50. doi: 10.1021/ol034370e.

Authors

Paul W R Harris¹, Margaret A Brimble, Peter D Gluckman

Affiliation

¹ NeuronZ Medicinal Chemistry Group, Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand.

PMID: 12762668
DOI: 10.1021/ol034370e

Abstract

[reaction: see text] 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis
Catalysis
Cyclization
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Conformation
Peptides, Cyclic / chemical synthesis*
Proline / chemical synthesis*
Stereoisomerism

Substances

Bridged Bicyclo Compounds
Indicators and Reagents
Peptides, Cyclic
Proline