Total syntheses of nobilamides B and D: Application of traceless Staudinger ligation

Tomoya Yamashita, Hiroaki Matoba, Takefumi Kuranaga, Masayuki Inoue

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Nobilamide B is a long-acting antagonist of transient receptor potential vanilloid-1 (TRPV1), and is expected to show therapeutic potential for treatment of pain. This linear heptapeptide possesses a Z-didehydroaminobutanoic acid moiety at the C-terminus. Stereoselective construction of the didehydroamino acid moiety was successfully achieved by application of the traceless Staudinger ligation. The combination of solid-phase peptide synthesis and the Staudinger ligation allowed rapid access to not only nobilamide B, but also its macrocyclic analogue nobilamide D.

Original languageEnglish
Pages (from-to)7746-7752
Number of pages7
JournalTetrahedron
Volume70
Issue number42
DOIs
Publication statusPublished - Oct 21 2014
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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