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首页> 外文期刊>Proceedings of the National Academy of Sciences of the United States of America >Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis
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Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis

机译：催化不对称全合成制备具有生物活性的疫霉交配激素

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摘要

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 α1. 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 α1. 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.
机译：使用我们最近开发的格氏试剂对映体选择性催化共轭加成方法，已合成了具有一系列1,5-甾体形成中心的疫霉交配激素。我们在非对映和对映选择性的迭代方法中应用了该方法，并获得了疫霉菌激素α1的16种可能的立体异构体中的两种。这些合成的立体异构体诱导了三种杂藻疫霉属P. infestans的A2交配型菌株中性孢子（卵孢子）的形成。 P. capsici和P. nicotianae，但不在A1交配型菌株中。反应是浓度依赖性的，卵孢子是可行的。这些结果证明了合成激素的生物活性类似于天然激素α1的生物活性。交配激素是各种生物体性生活周期中必不可少的组成部分。对于疫病菌等植物病原体而言，有性繁殖是遗传变异的重要来源。而且，厚壁的卵孢子是可以在恶劣的环境条件下生存的最耐用的繁殖体。有性生殖因此可以极大地影响疾病的流行。模仿疫霉菌交配激素活性的合成化合物的可用性将有助于进一步阐明这一重要的植物病原体群中的有性繁殖。

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