Journal of Organic Chemistry p. 5834 - 5838 (1985)
Update date:2022-08-03
Topics:
Kemp, D. S.
McNamara, Paul E.
Syntheses of the cyclic nonapeptides cyclo-(Gly-L-Cys(Bzl)-Gly)3, cyclo(L-Pro-Gly-L-Cys(Meb))3, and cyclo-(L-Cys(Meb)-LL-Acp)3 are described, where Meb = p=methoxybenzyl and Acp = 3-amino-2-piperidone-6-carboxylic acid, a β-turn-inducing dipeptide analogue.Removal of the S-blocking groups from each is described, followed by ring-forming reaction with 1,3,5-tris(bromomethylene)benzene to form an unusual series of relatively rigid vase-shaped cage compounds.Strong binding of three water molecules to the Acp-derived cage is reported.
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