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Synthesis and absolute configuration of hormone α1

Abstract

An important biological event in phytopathogens of the genus Phytophthora is sexual reproduction, which is conducted by two mating types, A1 and A2. A factor known as hormone α1 is secreted by the A1 mating type and induces the formation of sexual spores (oospores) in the A2 mating type. Here we describe the asymmetric synthesis and assignment of the absolute configuration of hormone α1 by oospore-inducing assays of the synthesized isomers.

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Figure 1: Physical and biological properties of the stereoisomers of hormone α1.

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Acknowledgements

The authors thank M. Ojika (Nagoya University) for valuable discussions and the copies of the NMR spectra of hormone α1, and T. Tashiro (RIKEN) and S. Kitamura (Nagoya University) for MS measurements. We are also grateful to M. Takenaka (Takasago International Co.) for his kind gift of citronellal, and to D.P. Curran (University of Pittsburg) and Weidong Li (Nankai University) for valuable discussions. This work was supported in part by grants from the Natural Science Foundation of China (20632030 and 20572072) and the Ministry of Education (New Century Excellent Teacher and the Research Fund for the Doctoral Program of Higher Education) of China (Y.Q.), and by a Grant for Faculty Research Projects from NODAI (Tokyo University of Agriculture) Research Institute (A.Y.).

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Contributions

X.Z. and N.K. contributed equally to this work. Y.Q., X.Z., X.X., J.W., D.Z. and Y.W. synthesized hormone α1 isomers E1aE1d, and A.Y. and N.K. synthesized hormone α1 isomers 1a1d. J.Q. and T.A. carried out the bioassays. A.Y., Y.Q., T.N., G.Y., J.Q. and Y.S. designed the project and wrote the manuscript. All authors discussed the results and commented on the manuscript.

Corresponding authors

Correspondence to Arata Yajima, Yong Qin or Jianhua Qi.

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Supplementary Figures 1–4, Supplementary Tables 1–4 and Supplementary Methods (PDF 6184 kb)

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Yajima, A., Qin, Y., Zhou, X. et al. Synthesis and absolute configuration of hormone α1. Nat Chem Biol 4, 235–237 (2008). https://doi.org/10.1038/nchembio.74

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