Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis

• DOI: 10.1073/pnas.0709289105
• Publication Date: 2008-06-17T01:11:20Z
• Authors: Syuzanna R. Harut...; Zhijian Zhao; Tim den Hartog; Klaas Bouwmeester; Adriaan J. Minnaard; Ben L. Feringa; Francine Govers
• Keywords: Heterothallic; Phytophthora capsici; Oospore; Sexual reproduction; Phytophthora infestans; Homothallism

A Phytophthora mating hormone with an array of 1,5-stereogenic centers has been synthesized by using our recently developed methodology catalytic enantioselective conjugate addition Grignard reagents. We applied this in a diastereo- and iterative route obtained two the 16 possible stereoisomers α1. These synthetic induced formation sexual spores (oospores) A2 type strains three heterothallic species, P. infestans , capsici nicotianae but not A1 strains. The response was concentration-dependent, oospores were viable. results demonstrate that biological activity resembles natural Mating hormones are essential components life cycle variety organisms. For plant pathogens like reproduction is important as source genetic variation. Moreover, thick-walled most durable propagules can survive harsh environmental conditions. Sexual thus greatly affect disease epidemics. availability compounds mimicking will be instrumental for further unravelling group pathogens.