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The second Phytophthora mating hormone defines interspecies biosynthetic crosstalk


The heterothallic species of the agricultural pest Phytophthora use mating hormones α1 and α2 to regulate their sexual reproduction. Here we describe the absolute stereostructure of the second mating hormone α2 as defined by spectroscopic analysis and total synthesis. We have uncovered not only the interspecies universality of α hormones but also the pathway by which α2 is biosynthesized from phytol by A2–mating type strains and metabolized to α1 by A1 strains.

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Figure 1: Production and stereochemical determination of α2.
Figure 2: Biosynthetic pathway of α hormones.

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We thank K. Kawakita for P. infestans strains and W.H. Ko for valuable suggestions. This work was supported by Grants-in-Aid for Scientific Research from Japan Society for the Promotion of Science (22248012, 21710239 and 18380073). S.D.M. is a recipient of a Japanese Ministry of Education, Culture, Sports, Science and Technology (MEXT) scholarship (080028).

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M.O. designed the project and wrote the manuscript; S.D.M. isolated 2, tested hormone response and prepared the manuscript; H.K. isolated 2; A.Y., K.T. and T.N. performed chemical syntheses; H.M. did isotope-labeled experiments; R.M. contributed to LC/MS analysis; T.A. contributed to bioassay; J.Q. isolated 1; and Y.S. designed the project.

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Correspondence to Makoto Ojika.

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The authors declare no competing financial interests.

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Ojika, M., Molli, S., Kanazawa, H. et al. The second Phytophthora mating hormone defines interspecies biosynthetic crosstalk. Nat Chem Biol 7, 591–593 (2011).

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