Synthesis of orthogonally protected thioamide dipeptides for use in solid-phase peptide synthesis

Kim Manzor, Fintan Kelleher

Research output: Contribution to journalArticlepeer-review

Abstract

Orthogonally protected thioamide-containing dipeptides were efficiently and cleanly prepared from the precursor dipeptides using Curphey's method (P4S10, hexamethyldisiloxane (HMDO), reflux, DCM) in 67–96% isolated yield. This was in contrast to the use of Lawesson's or Berzelius’ reagents where significant issues with reaction non-completion, decomposition and purification were observed. Subsequent clean removal of the dipeptides’ t-butyl ester protecting groups gave thioamide dipeptide acids which were suitable for use in solid-phase peptide synthesis (SPPS).

Original languageEnglish
Pages (from-to)5237-5239
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number47
DOIs
Publication statusPublished - 2016

Keywords

  • Curphey's method
  • Thioamide
  • Thionation
  • Thiopeptides

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