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

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

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...

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Veröffentlicht in:Organic letters 2015-07, Vol.17 (14), p.3636-3639
Hauptverfasser: Raibaut, Laurent, Drobecq, Hervé, Melnyk, Oleg
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Chalcogens - chemical synthesis
Chalcogens - chemistry
Cysteine - chemistry
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
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container_title Organic letters
container_volume 17
creator Raibaut, Laurent
Drobecq, Hervé
Melnyk, Oleg
description 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.
doi_str_mv 10.1021/acs.orglett.5b01817
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subjects Amides - chemistry
Chalcogens - chemical synthesis
Chalcogens - chemistry
Cysteine - chemistry
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
title Selectively Activatable Latent Thiol and Selenolesters Simplify the Access to Cyclic or Branched Peptide Scaffolds
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