Journal article
(+)-Geodin from Aspergillus terreus
Organic Chemistry, Department of Chemistry, Technical University of Denmark1
Department of Chemistry, Technical University of Denmark2
Center for Microbial Biotechnology, Department of Systems Biology, Technical University of Denmark3
Department of Systems Biology, Technical University of Denmark4
Heidelberg University 5
X-ray Crystallography, Department of Chemistry, Technical University of Denmark6
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], C(17)H(12)Cl(2)O(7), 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 2(1) screw axis. Molecules denoted 2 interact through an O...Cl halogen bond, also creating chains of molecules parallel to the crystallographic 2(1) 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.
Language: | English |
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Year: | 2011 |
Pages: | o125-8 |
ISSN: | 16005759 and 01082701 |
Types: | Journal article |
DOI: | 10.1107/S0108270111005816 |
ORCIDs: | Mortensen, Uffe Hasbro , Clausen, Mads Hartvig , Larsen, Thomas Ostenfeld and Harris, Pernille |