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Chem
- Publisher
- Wiley
- Copyright
- © 2018 Wiley Periodicals, Inc.
- eISSN
- 2475-8817
- DOI
- 10.1002/pep2.24042
- Publisher site
- See Article on Publisher Site
Abstract
The total syntheses of the naturally occurring cyclic pentapeptides, segetalins B and G, using a traceless pseudoproline‐mediated cyclization reaction is reported. The incorporation of a cysteine‐derived gem‐dimethyl pseudoproline [Cys(ΨMe,MePro)] residue in the linear precursors to induce a cisoid amide bond prior to the head‐to‐tail cyclization resulted in improved cyclization yields in both cases. Cysteine‐derived pseudoproline residues lacking the gem‐dimethyl substituents [Cys(ΨH,HPro)] were not as effective at inducing cisoid conformations of the amide bonds and resulted in lower cyclization yields with a concomitant increase in the formation of cyclodimers. The Cys(ΨMe,MePro) containing cyclic peptides were subject to deprotection and desulfurization to give the alanine containing natural products in high overall yields. In contrast, deprotection of cyclic peptides containing Cys(ΨH,HPro) residues upon treatment with trifluoroacetic acid removed other side chain‐protecting groups but left the Cys(ΨH,HPro) residues intact.
Journal
Peptide Science – Wiley
Published: May 1, 2018
Keywords: ; ;