Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis.
A Phytophthora mating hormone with an array of 1,5-stereogenic centers has been synthesized by using our recently developed methodology of catalytic enantioselective conjugate addition of Grignard reagents. We applied this methodology in a diastereo- and enantioselective iterative route and obtained two of the 16 possible stereoisomers of Phytophthora hormone alpha1. These synthetic stereoisomers induced the formation of sexual spores (oospores) in A2 mating type strains of three heterothallic Phytophthora species, P. infestans, P. capsici, and P. nicotianae but not in A1 mating type strains. The response was concentration-dependent, and the oospores were viable. These results demonstrate that the biological activity of the synthetic hormone resembles that of the natural hormone alpha1. Mating hormones are essential components in the sexual life cycle of a variety of organisms. For plant pathogens like Phytophthora, sexual reproduction is important as a source of genetic variation. Moreover, the thick-walled oospores are the most durable propagules that can survive harsh environmental conditions. Sexual reproduction can thus greatly affect disease epidemics. The availability of synthetic compounds mimicking the activity of Phytophthora mating hormone will be instrumental for further unravelling sexual reproduction in this important group of plant pathogens.
Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Syuzanna R
SR
Harutyunyan
Zhijian
Z
Zhao
Tim den
Td
Hartog
Klaas
K
Bouwmeester
Adriaan J
AJ
Minnaard
Ben L
BL
Feringa
Francine
F
Govers
D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D010838:Phytophthora / Q000254:growth & development / Q000378:metabolism*; D013170:Spores / Q000254:growth & development; D013237:Stereoisomerism
D004224:Diterpenes; C504077:mating hormone alpha1, Phytophthora