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Issue 8, 1993
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Iron uptake system of some members of the genus tolypocladium: crystal structure of the ligand and its iron(III) complex

Abstract

A new type of fungal hydroxamic acid (1′S,2′R,4′S,6′R)-3-(2′,4′-dimethyl-6′-vinylcyclohexyl)-1,4-dihydroxy-2(1H)-pyridone (tolypocin, HL) has been isolated from the mycelium of the fungus Tolypocladium geodes. The acid (C15H21NO3) crystallized from methanol [monoclinic, space group P21, Z= 4, a= 12.28(1), b= 9.958(5), c= 12.737(4), Å, β= 94.91(5)°]. The structure was solved by direct methods and refined to a final R value of 0.055 for 2393 unique observed reflections. The iron(III) trischelate complex of this ligand [FeL3] has been isolated from the mycelium of the fungus Tolypocladium terricola. Its methanol solvate (C45H60FeN3O9·2MeOH) was crystallized from methanol [orthorhombic, space group P212121, Z= 4, a= 20.27(3), b= 19.35(5), c= 13.43(4)Å]. The structure was solved by direct methods and refined to a final R value of 0.062 for 5562 observed reflections. The absolute configuration of the complex as determined from CD spectra and anomalous X-ray dispersion has been shown to be Λ-cis both in solution and in the solid state.

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Article type: Paper
DOI: 10.1039/DT9930001287
Citation: J. Chem. Soc., Dalton Trans., 1993, 1287-1293
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    Iron uptake system of some members of the genus tolypocladium: crystal structure of the ligand and its iron(III) complex

    A. Jegorov, V. Maťha, M. Hušák, B. Kratochvíl, J. Stuchlík, P. Sedmera and V. Havlíček, J. Chem. Soc., Dalton Trans., 1993, 1287
    DOI: 10.1039/DT9930001287

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