HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Rieder, C. Articles by Eisenreich, W. Search for Related Content PubMed PubMed Citation Articles by Rieder, C. Articles by Eisenreich, W. Social Bookmarking                      What's this?

J Biol Chem, Vol. 273, Issue 29, 18099-18108, July 17, 1998

Biosynthesis of the Diterpene Verrucosan-2-ol in the Phototrophic Eubacterium Chloroflexus aurantiacus
A RETROBIOSYNTHETIC NMR STUDY

Christoph Rieder, Gerhard Strauß^§, Georg Fuchs^§, Duilio Arigoni^¶, Adelbert Bacher, and Wolfgang Eisenreich

From the  Department of Organic Chemistry and Biochemistry, Technische Universität München, Lichtenbergstraße 4, D-85747 Garching, Germany and ^§ Microbiology, Faculty of Biology, Albert-Ludwigs-Universität Freiburg, Schänzlestraße 1, D-79104 Freiburg, Germany, and ^¶ Laboratory of Organic Chemistry, Eidgenössische Technische Hochschule Zürich, Universitätsstraße 16, CH-8092 Zürich, Switzerland

The biosynthesis of verrucosan-2-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-2-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-2-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.

CiteULike

Complore

Connotea

Del.icio.us

Digg

Reddit

Technorati

This article has been cited by other articles:

				J. M. Hayes and J. M. Hayes Fractionation of Carbon and Hydrogen Isotopes in Biosynthetic Processes Reviews in Mineralogy and Geochemistry, January 1, 2001; 43(1): 225 - 277. [Full Text] [PDF]

				B. M. Lange, T. Rujan, W. Martin, and R. Croteau Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes PNAS, November 8, 2000; (2000) 240454797. [Abstract] [Full Text]

				W. Eisenreich, C. Rieder, C. Grammes, G. He{beta}ler, K.-P. Adam, H. Becker, D. Arigoni, and A. Bacher Biosynthesis of a Neo-epi-verrucosane Diterpene in the Liverwort Fossombronia alaskana. A RETROBIOSYNTHETIC NMR STUDY J. Biol. Chem., December 17, 1999; 274(51): 36312 - 36320. [Abstract] [Full Text] [PDF]

				M. T. J. van der Meer, S. Schouten, B. E. van Dongen, W. I. C. Rijpstra, G. Fuchs, J. S. S. Damste, J. W. de Leeuw, and D. M. Ward Biosynthetic Controls on the 13C Contents of Organic Components in the Photoautotrophic Bacterium Chloroflexus aurantiacus J. Biol. Chem., March 30, 2001; 276(14): 10971 - 10976. [Abstract] [Full Text] [PDF]

				B. M. Lange, T. Rujan, W. Martin, and R. Croteau Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes PNAS, November 21, 2000; 97(24): 13172 - 13177. [Abstract] [Full Text] [PDF]