Synthesis and conformational analysis of cyclic analogues of inverse gamma-turns.
Gamma-turn analogues comprising a modified dipeptide constrained in an eleven-membered ring were prepared by alkene metathesis and analysed by NMR and molecular modelling studies. The results reveal that some of the cyclic analogues form inverse gamma-turns and preferentially adopt conformations determined by the identity of the incorporated amino acid residues and the nature of the constraining linker (E/Z-alkene or alkane).
Kaewpet
Morakot
M
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, UK OX1 3TA.
Odell
Barbara
B
King
Michael A
MA
Banerji
Biswadip
B
Schofield
Christopher J
CJ
Claridge
Timothy D W
TD
D000475:Alkenes / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D002264:Carboxylic Acids; D004151:Dipeptides; D010456:Peptides, Cyclic