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 language | English |
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Pages (from-to) | 7746-7752 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 70 |
Issue number | 42 |
DOIs | |
Publication status | Published - 2014 Oct 21 |
Externally published | Yes |
Keywords
- Peptides
- Solid-phase synthesis
- Staudinger ligation
- Total synthesis
- TRPV1 antagonist
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry