Lüttenberg Sebastian, Sondermann Frank, Scherkenbeck Jürgen
Bergische Universität Wuppertal, Fachgruppe Chemie, Gaußstraße 20, D-42119 Wuppertal, Germany.
Tetrahedron. 2012 Feb 25;68(8):2068-2073. doi: 10.1016/j.tet.2011.12.026. Epub 2011 Dec 16.
Cyclodepsipeptides of the enniation-, PF1022-, and verticilide-family represent a diverse class of highly interesting natural products with respect to their manifold biological activities. However, until now no stepwise solid-phase synthesis has been accomplished due to the difficult combination of -methyl amino acids and hydroxycarboxylic acids. We report here the first stepwise solid-phase synthesis of the anthelmintic cyclooctadepsipeptide PF1022A based on an Fmoc/THP-ether protecting group strategy on Wang-resin. The standard conditions of our synthesis allow an unproblematic adaption to an automated peptide synthesizer.
恩镰孢菌素、PF1022和轮枝菌素家族的环缩肽是一类极具吸引力的天然产物，具有多种生物活性。然而，由于α-甲基氨基酸和羟基羧酸难以组合，迄今为止尚未完成逐步固相合成。我们在此报告基于Wang树脂上的Fmoc/THP-醚保护基策略，首次逐步固相合成驱虫环辛缩肽PF1022A。我们合成的标准条件可毫无问题地适用于自动肽合成仪。
