Crystal structure of diaphorin methanol monosolvate isolated from Diaphorina citri Kuwayama, the insect vector of citrus greening disease
| Autor: | John S Ramsey, Doletha M. E. Szebenyi, M.L. Heck, D.G. Hall, Kevin J. Howe, Irina A. Kriksunov, Stuart B. Krasnoff |
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| Rok vydání: | 2018 |
| Předmět: |
diaphorin
0301 basic medicine crystal structure Stereochemistry Diaphorina citri Pederin Crystal structure 010402 general chemistry 01 natural sciences Research Communications 03 medical and health sciences chemistry.chemical_compound ‘Candidatus Profftella armatura’ General Materials Science Crystallography biology Absolute configuration General Chemistry hydrogen bonding Condensed Matter Physics biology.organism_classification pederin 0104 chemical sciences 030104 developmental biology chemistry QD901-999 Aminal Citrus greening disease `Candidatus Profftella armatura' Derivative (chemistry) Acetamide |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications, Vol 74, Iss 4, Pp 445-449 (2018) Acta Crystallographica Section E: Crystallographic Communications |
| ISSN: | 2056-9890 |
| Popis: | ‘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. The relative configurations of three out of its nine stereogenic centers, which could not be determined by NMR, were assigned based on the crystal structure. The title compound C22H39NO9·CH3OH [systematic name: (S)-N-((S)-{(2S,4R,6R)-6-[(S)-2,3-dihydroxypropyl]-4-hydroxy-5,5-dimethyltetrahydro-2H-pyran-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 ▸). 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-bromobenzoate derivative of pederin, a biogenically related compound whose crystal structure was reported previously [Furusaki et al. (1968 ▸). Tetrahedron Lett. 9, 6301–6304]. Thus, the absolute configuration of diaphorin is proposed by analogy to that of pederin. |
| Databáze: | OpenAIRE |
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