Work

Biosynthesis of the Diterpene Verrucosan-2β-ol in the Phototrophic Eubacterium Chloroflexus aurantiacus

Year: 1998

Type: article

Abstract: The biosynthesis of verrucosan-2beta-ol in the green phototrophic eubacterium Chloroflexus aurantiacus was investigated by in vivo incorporation of singly or doubly 13C-labeled acetate. The 13C labeling of the isolated diterpene was analyzed by one- and two-dimensional NMR spectroscopy. The 13C-labeling patterns of verrucosan-2beta-ol were compared with the labeling patterns of intermediary metabolites (acetyl-CoA, pyruvate, and glyceraldehyde 3-phosphate) which were deduced from amino acids and nucleosides by retrobiosynthetic analysis. The results show that verrucosan-2beta-ol is synthesized via mevalonate and not via the deoxyxylulose pathway, which was discovered recently in some eubacteria, algae, and plants. A scheme for the formation of the unusual tetracyclic ring system is offered. The cyclization process is initiated by the solvolysis of pyrophosphate from geranyllinaloyl pyrophosphate and the mechanism involves a Wagner-Meerwein rearrangement, a 1,5-hydride shift, and a cyclopropylcarbinyl to cyclopropylcarbinyl rearrangement.

Source: Journal of Biological Chemistry

DOI: 10.1074/jbc.273.29.18099

Authors: Christoph Rieder, Gerhard Strauß, Georg Fuchs, Duilio Arigoni, Adelbert Bacher, Wolfgang Eisenreich

Institutions: Technical University of Munich, University of Freiburg, ETH Zurich, Laboratory of Organic Chemistry

Language: English

Topic: Plant biochemistry and biosynthesis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $3,430

Funder: Deutsche Forschungsgemeinschaft