Synthesis of cyclic peptides via O– N-acyl migration

We describe here a novel and convenient synthesis of head-to-tail cyclic peptide avoiding racemization. Linear depsipeptides including a serine residue as the key element for ester bond formation and acyl transfer were synthesized on 2-chlorotrityl chloride resin. After cleavage from the resin, intr...

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Bibliographic Details
Published in:Tetrahedron letters 2008-07, Vol.49 (31), p.4674-4676
Main Authors: Lécaillon, Jennifer, Gilles, Pierre, Subra, Gilles, Martinez, Jean, Amblard, Muriel
Format: Article
Language:English
Subjects:
Cyclic peptides
Depsipeptides
Epimerization-free
O– N-Acyl migration
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Summary:We describe here a novel and convenient synthesis of head-to-tail cyclic peptide avoiding racemization. Linear depsipeptides including a serine residue as the key element for ester bond formation and acyl transfer were synthesized on 2-chlorotrityl chloride resin. After cleavage from the resin, intramolecular head-to-tail cyclization was performed in solution by C-terminal activation of urethane protected O-acyl serine residue. After removal of the N α-serine protecting group, the final step consisted in O– N-acyl migration reaction on the ‘switch’ or ‘click’ element to restore native cyclic peptides.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.05.049