Peptide cyclization via ring-closing metathesis: the N-alkenoxy peptide approach.
The preparation of cyclic hexapeptides from N-hydroxy tripeptides building blocks is described. Introduction of an unsaturated chain on the hydroxamate oxygen followed by fragment coupling leads to N,N'-dialkenoxy hexapeptides that are efficiently cyclized through a ring-closing metathesis reaction. The length of the alkene chains allows the modulation of the ring size: the synthesis of 17- and 18-membered cycles is reported.
Lawrence
James
J
Département de Chimie Moléculaire, UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP-53, 38041, Grenoble Cedex 9, France.
Jourdan
Muriel
M
Vallée
Yannick
Y
Blandin
Véronique
V
D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D005240:Feasibility Studies; D006878:Hydroxides / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry*
D000475:Alkenes; D006878:Hydroxides; D009842:Oligopeptides; C031356:hydroxide ion; D009584:Nitrogen