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Pterulamides I−VI, Linear Peptides from a Malaysian Pterula sp.

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journal contribution
posted on 27.10.2006 by Gerhard Lang, Maya I. Mitova, Anthony L. J. Cole, Laily B. Din, Sabaratnam Vikineswary, Noorlidah Abdullah, John W. Blunt, Murray H. G. Munro
Six new linear peptides, pterulamides I−VI (16), were isolated from the fruiting bodies of a Malaysian Pterula species. The structures were elucidated by MS and 2D NMR experiments, and the absolute configurations of the constituent amino acids established using Marfey's method. The pterulamides are mainly assembled from nonpolar N-methylated amino acids and, most interestingly, have non-amino-acid N-terminal groups, among them the unusual cinnamoyl, (E)-3-methylsulfinylpropenoyl, and (E)-3-methylthiopropenoyl groups. Furthermore, pterulamides I−V are the first natural peptides with a methylamide C-terminus. Pterulamides I and IV are cytotoxic against the P388 cell line with IC50 values of 0.55 and 0.95 μg/mL (0.79 and 1.33 μM), respectively.