Synthesis of cyclic proline-containing peptides via ring-closing metathesis.
[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.
Harris
Paul W R
PW
NeuronZ Medicinal Chemistry Group, Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand.
Brimble
Margaret A
MA
Gluckman
Peter D
PD
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D011392:Proline / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D010456:Peptides, Cyclic; D011392:Proline