American Chemical Society
ol5b01817_si_001.pdf (1.38 MB)

Selectively Activatable Latent Thiol and Selenolesters Simplify the Access to Cyclic or Branched Peptide Scaffolds

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journal contribution
posted on 2015-07-17, 00:00 authored by Laurent Raibaut, Hervé Drobecq, Oleg Melnyk
The cyclic dichalcogenides based on the bis­(2-chalcogenoethyl)­amide structure are latent N,S (SEA, chalcogen = S) or N,Se (SeEA, chalcogen = Se) acyl shift systems. The large difference in the reducing potential between SEA and SeEA dichalcogenides allows their sequential and selective activation by reduction. Based on these concepts, one-pot three or four peptide segment assembly processes were designed, facilitating access to branched or cyclic peptide scaffolds.