(+)-Geodin from Aspergillus terreus
The fungal metabolite (+)-geodin [systematic name: (2R)-methyl 5,7-dichloro-4-hydroxy-6′-methoxy-6-methyl-3,4′-dioxospiro[benzofuran-2,1′-cyclohexa-2′,5′-diene]-2′-carboxylate], C17H12Cl2O7, was isolated from Aspergillus terreus. The crystal structure contains two independent molecules in th...
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| Hauptverfasser: | , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
23 February 2011
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| In: |
Acta crystallographica. Section C, Structural Chemistry
Year: 2011, Jahrgang: 67, Heft: 3, Pages: o125-o128 |
| ISSN: | 2053-2296 |
| DOI: | 10.1107/S0108270111005816 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1107/S0108270111005816 Verlag, lizenzpflichtig, Volltext: http://scripts.iucr.org/cgi-bin/paper?lg3050 
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| Verfasserangaben: | Mads H. Rønnest, Morten T. Nielsen, Blanka Leber, Uffe H. Mortensen, Alwin Krämer, Mads H. Clausen, Thomas O. Larsen and Pernille Harris |
| Zusammenfassung: | The fungal metabolite (+)-geodin [systematic name: (2R)-methyl 5,7-dichloro-4-hydroxy-6′-methoxy-6-methyl-3,4′-dioxospiro[benzofuran-2,1′-cyclohexa-2′,5′-diene]-2′-carboxylate], C17H12Cl2O7, was isolated from Aspergillus terreus. The crystal structure contains two independent molecules in the asymmetric unit. Molecules denoted 1 interact through O—H⋯O hydrogen bonds creating chains of molecules parallel to the crystallographic 21 screw axis. Molecules denoted 2 interact through an O⋯Cl halogen bond, also creating chains of molecules parallel to the crystallographic 21 screw axis. Molecules 1 and 2 interact through another O⋯Cl halogen bond. The two molecules are similar but molecules 2 have a slightly more planar cyclohexadiene ring than molecules 1. The absolute structure of (+)-geodin has been unequivocally assigned with the spiro centre having the R configuration in both molecules. The structurally related (+)-griseofulvin has an S configuration at the spiro centre, a difference of potential biological and biosynthetic relevance. |
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| Beschreibung: | Gesehen am 19.09.2022 |
| Beschreibung: | Online Resource |
| ISSN: | 2053-2296 |
| DOI: | 10.1107/S0108270111005816 |