Flexible synthesis and evaluation of diverse anti-Apicomplexa cyclic peptides

J Org Chem. 2013 Mar 27. [Epub ahead of print]

Flexible synthesis and evaluation of diverse anti-Apicomplexa cyclic peptides

Traoré M, Mietton F, Maubon D, Peuchmaur M, Francisco Hilario F, Pereira de Freitas R, Bougdour A, Curt A, Maynadier M, Vial H, Pelloux H, Hakimi MA, Wong YS.

A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed and takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only few steps (1-3 steps). The diversification processes make use of selective radical coupling reactions and involve a new example of reductive carbon-nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

 PMID: 23535138 [PubMed - as supplied by publisher]