Abstract
Cyclochlorotine (CCT) is a toxic metabolite of Penicillium islandicum Sopp, having the structure of cyclo(‐L‐Ser‐L‐β‐Phe‐L‐Ser‐L‐Pro(Cl2)‐L‐Abu‐). An analog of CCT, cyclo(‐L‐Ser‐L‐β‐Phe‐L‐Ser‐L‐Pro(Cl)‐L‐Abu‐) ([L‐Pro(Cl)4]CCT, 1), has been synthesized by the conventional method for peptide synthesis in order to study possible toxic activity of 1. Peptide 1 showed no toxicity toward several microorganisms and mice. 1H‐N.m.r. and CD studies on 1 indicate that the conformation of 1 in solution is similar to that of crystalline CCT. These results suggest that 3‐cis‐chlorine moiety of Pro(Cl2) in CCT plays an essential role in biological activities.
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