Structure of Reductiomycin

Agricultural and Biological Chemistry
1980.0

Abstract

The structure of the novel antibiotic reductiomycin, isolated from Streptomyces griseorubiginosus nov. sp. and exhibiting antiviral and antifungal activities, was clarified by X-ray diffraction studies. Since its structure could not be unequivocally determined from spectroscopic data alone, the direct method using MULTAN was employed. The solution was based on 310 reflexions with |E₀| ≥ 1.30, and the E map with the lowest RKarle (28.0) revealed 22 non-hydrogen atoms. All atoms were located via successive Fourier, difference Fourier, and least-squares methods. Refinement was carried out by the block-diagonal least-squares method with anisotropic temperature factors for non-hydrogen atoms, resulting in a final R value of 0.098. Oxygen and nitrogen atoms were identified from temperature factor behavior, and hydrogen atoms were found on a difference Fourier map. Reductiomycin has a unique chemical structure with a strong intramolecular hydrogen bond (O...O distance: 2.509 A). The molecule is approximately planar except for the acetoxy group (dihedral angle of 76.5° between the main plane and acetoxy group plane), and its absolute configuration was not determined. The crystal structure viewed along the c-axis shows an intermolecular contact O(5)[1]...C(7)[2] of 3.15 A.

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