Diverted total synthesis of falcitidin acyl tetrapeptides as new antimalarial leads

Kotturi, Santosh R., Somanadhan, Brinda, Ch'Ng, Jun-Hong, Tan, Kevin S.-W., Butler, Mark S. and Lear, Martin J. (2014) Diverted total synthesis of falcitidin acyl tetrapeptides as new antimalarial leads. Tetrahedron Letters, 55 11: 1949-1951. doi:10.1016/j.tetlet.2014.02.008


Author Kotturi, Santosh R.
Somanadhan, Brinda
Ch'Ng, Jun-Hong
Tan, Kevin S.-W.
Butler, Mark S.
Lear, Martin J.
Title Diverted total synthesis of falcitidin acyl tetrapeptides as new antimalarial leads
Journal name Tetrahedron Letters   Check publisher's open access policy
ISSN 0040-4039
1873-3581
Publication date 2014-03-12
Year available 2014
Sub-type Article (original research)
DOI 10.1016/j.tetlet.2014.02.008
Volume 55
Issue 11
Start page 1949
End page 1951
Total pages 3
Place of publication Oxford, United Kingdom
Publisher Pergamon Press
Language eng
Formatted abstract
We report not only the convergent total synthesis of falcitidin, a natural inhibitor of falcipain-2 from myxobacterium Chitinophaga, but also its diversification into a new antimalarial class of N-acyl tetrapeptides (Acyl-His-Ile-Val-Pro-NH2). Despite the lack of whole-cell activity of falcitidin itself, our study led to the identification of a trifluoromethyl (CF3) analogue displaying sub-micromolar IC50 activity against Plasmodium falciparum 3D7 in a standard blood-cell assay, but only when N-tritylated on its histidine (imidazole) residue.
Keyword Falcitidin
Tetrapeptide
Trifluoromethyl
Natural products
Antimalarial agents
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
Official Audit
Institute for Molecular Bioscience - Publications
 
Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 1 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 1 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Created: Tue, 08 Apr 2014, 10:23:30 EST by System User on behalf of Institute for Molecular Bioscience