Crystal structure of diaphorin methanol monosolvate isolated from Diaphorina citri Kuwayama, the insect vector of citrus greening disease

Acta Crystallographica. Section E, Crystallographic Communications
D Marian SzebenyiStuart B Krasnoff

Abstract

The title compound C22H39NO9·CH3OH [systematic name: (S)-N-((S)-{(2S,4R,6R)-6-[(S)-2,3-di-hydroxy-prop-yl]-4-hy-droxy-5,5-di-methyl-tetra-hydro-2H-pyran-2-yl}(hy-droxy)meth-yl)-2-hy-droxy-2-[(2R,5R,6R)-2-meth-oxy-5,6-dimeth-yl-4-methyl-ene-tetra-hydro-2H-pyran-2-yl]acetamide methanol monosolvate], was isolated from the Asian citrus psyllid, Diaphorina citri Kuwayama, and crystallizes in the space group P21. 'Candidatus Profftella armatura' a bacterial endosymbiont of D. citri, biosynthesizes diaphorin, which is a hybrid polyketide-nonribosomal peptide comprising two highly substituted tetra-hydro-pyran rings joined by an N-acyl aminal bridge [Nakabachi et al. (2013 ▸). Curr. Biol.23, 1478-1484]. The crystal structure of the title compound establishes the complete relative configuration of diaphorin, which agrees at all nine chiral centers with the structure of the methanol monosolvate of the di-p-bromo-benzoate derivative of pederin, a biogenically related compound whose crystal structure was reported previously [Furusaki et al. (1968 ▸). Tetra-hedron Lett.9, 6301-6304]. Thus, the absolute configuration of diaphorin is proposed by analogy to that of pederin.

References

Mar 25, 1999·Acta Crystallographica. Section D, Biological Crystallography·C M Weeks, R Miller
Oct 17, 2002·Proceedings of the National Academy of Sciences of the United States of America·Jörn Piel
May 1, 1997·Journal of Synchrotron Radiation·D M SzebenyiC Nielsen
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
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Apr 13, 2010·Acta Crystallographica. Section D, Biological Crystallography·P EmsleyK Cowtan
Jul 16, 2013·Current Biology : CB·Atsushi NakabachiTakema Fukatsu
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward

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