(+)-Geodin from Aspergillus terreus.

Publication: Research - peer-reviewJournal article – Annual report year: 2011

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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.
Original languageEnglish
JournalActa Crystallographica. Section C: Crystal Structure Communications
Publication date2011
Volume67
Journal numberPt 3
Pageso125-o128
ISSN0108-2701
DOIs
StatePublished

Bibliographical note

© 2011 International Union of Crystallography

CitationsWeb of Science® Times Cited: 5
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