Enzyme-Catalyzed Rearrangement of a Diepoxy-germacrane Compound into New 7-epi-Eudesmane Derivatives

Two new 7-epi-eudesmane derivatives, together with two new germacrane compounds, have been isolated from the microbial-transformation of a (1α,10β),(4β,5α)-diepoxygermacrane using the hydroxylating fungi Rhizopus nigricans. The rearranged skeleton and the stereochemistry of the chiral centers have b...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-01, Vol.70 (1), p.338-341
Main Authors: García-Granados, Andrés, Gutiérrez, María C, Martínez, Antonio, Rivas, Francisco
Format: Article
Language:English
Subjects:
Biological and medical sciences
Biotransformation
Catalysis
Fundamental and applied biological sciences. Psychology
Mechanisms. Catalysis. Electron transfer. Models
Molecular biophysics
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Physical chemistry in biology
Rhizopus - enzymology
Rhizopus - metabolism
Sesquiterpenes, Eudesmane - chemical synthesis
Sesquiterpenes, Eudesmane - chemistry
Sesquiterpenes, Germacrane - chemistry
Stereoisomerism
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Summary:Two new 7-epi-eudesmane derivatives, together with two new germacrane compounds, have been isolated from the microbial-transformation of a (1α,10β),(4β,5α)-diepoxygermacrane using the hydroxylating fungi Rhizopus nigricans. The rearranged skeleton and the stereochemistry of the chiral centers have been determined by means of their spectral data, and the absolute configuration has been confirmed by single-crystal X-ray analyses. A possible mechanism based on an enzyme-catalyzed isomerization to a 1α-hydroxy-(4β,5α)-epoxygermacr-9(E)-ene intermediate and a subsequent cyclization process is proposed in order to explain the formation of the 7-epi-eudesmane compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048783k