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.
Highlights
The title compound C22H39NO9ÁCH3OH [systematic name: (S)-N-((S){(2S,4R,6R)-6-[(S)-2,3-dihydroxypropyl]-4-hydroxy-5,5-dimethyltetrahydro-2Hpyran-2-yl}(hydroxy)methyl)-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-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 tetrahydropyran rings joined by an N-acyl aminal bridge [Nakabachi et al (2013)
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-bromobenzoate derivative of pederin, a biogenically related compound whose crystal structure was reported previously [Furusaki et al (1968)
Summary
Huanglongbing (HLB), known as citrus greening disease, which destroys the marketability of citrus fruit and eventually kills the tree, is a major threat to world citrus production (Wang et al, 2017; Bove, 2006). A complex community of vertically transmitted endosymbiotic bacteria colonizes D. citri, whether or not the psyllids are infected with ‘Ca. L. asiaticus’ (Nakabachi et al, 2013). Two of these D. citri endosymbionts, ‘Candidatus Profftella armatura’, and ‘Candidatus Carsonella rudii’ are localized to the bacteriome, an organ in the D. citri abdomen (Nakabachi et al, 2013).
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
