| Autor: |
Szebenyi DM; Cornell High Energy Synchrotron Source, Cornell University, Ithaca, NY 14853, USA., Kriksunov I; Cornell High Energy Synchrotron Source, Cornell University, Ithaca, NY 14853, USA., Howe KJ; USDA-ARS RW Holley Center for Agriculture and Health, Ithaca NY 14853, USA., Ramsey JS; USDA-ARS RW Holley Center for Agriculture and Health, Ithaca NY 14853, USA., Hall DG; U.S. Horticultural Research Laboratory, Fort Pierce, FL 34945, USA., Heck ML; USDA-ARS RW Holley Center for Agriculture and Health, Ithaca NY 14853, USA.; Boyce Thompson Institute for Plant Research, Ithaca, NY 14853, USA.; Plant Pathology and Plant-Microbe Biology Section, Cornell University, Ithaca, NY 14853, USA., Krasnoff SB; USDA-ARS RW Holley Center for Agriculture and Health, Ithaca NY 14853, USA. |
| Abstrakt: |
The title compound C 22 H 39 NO 9 ·CH 3 OH [systematic name: ( S )- N -(( S )-{(2 S ,4 R ,6 R )-6-[( S )-2,3-di-hydroxy-prop-yl]-4-hy-droxy-5,5-di-methyl-tetra-hydro-2 H -pyran-2-yl}(hy-droxy)meth-yl)-2-hy-droxy-2-[(2 R ,5 R ,6 R )-2-meth-oxy-5,6-dimeth-yl-4-methyl-ene-tetra-hydro-2 H -pyran-2-yl]acetamide methanol monosolvate], was isolated from the Asian citrus psyllid, Diaphorina citri Kuwayama, and crystallizes in the space group P 2 1 . ' 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. |
