Activation-Independent Cyclization of Monoterpenoids-Reference-Cited by-同舟云学术

Activation-Independent Cyclization of Monoterpenoids

Published:2012-02-15 Issue:4 Volume:78 Page:1055-1062
ISSN:0099-2240
Container-title:Applied and Environmental Microbiology
language:en
Short-container-title:Appl Environ Microbiol

Author:

Siedenburg Gabriele¹,Jendrossek Dieter¹,Breuer Michael²,Juhl Benjamin³,Pleiss Jürgen³,Seitz Miriam³,Klebensberger Janosch³,Hauer Bernhard³

Affiliation:

1. Institute of Microbiology, University of Stuttgart, Stuttgart, Germany

2. Fine Chemicals and Biocatalysis Research, BASFSE, Ludwigshafen, Germany

3. Institute of Technical Biochemistry, University of Stuttgart, Stuttgart, Germany

Abstract

ABSTRACT The biosynthesis of cyclic monoterpenes (C 10 ) generally requires the cyclization of an activated linear precursor (geranyldiphosphate) by specific terpene cyclases. Cyclic triterpenes (C 30 ), on the other hand, originate from the linear precursor squalene by the action of squalene-hopene cyclases (SHCs) or oxidosqualene cyclases (OSCs). Here, we report a novel terpene cyclase from Zymomonas mobilis (ZMO1548-Shc) with the unique capability to cyclize citronellal to isopulegol. To our knowledge, ZMO1548-Shc is the first biocatalyst with diphosphate-independent monoterpenoid cyclase activity. A combinatorial approach using site-directed mutagenesis and modeling of the active site with a bound substrate revealed that the cyclization of citronellal proceeds via a different mechanism than that of the cyclization of squalene.

Publisher

American Society for Microbiology

Subject

Ecology,Applied Microbiology and Biotechnology,Food Science,Biotechnology

Link

https://journals.asm.org/doi/pdf/10.1128/AEM.07059-11

Reference35 articles.

1. Plant terpenoid synthases: molecular biology and phylogenetic analysis;Bohlmann J;Proc. Natl. Acad. Sci. U. S. A.,1998

2. Protein structure prediction servers at University College London

3. Cyclisation of citronellal to isopulegol catalysed by hydrous zirconia and other solid acids;Chuah GK;J. Catal.,2001

4. One pot synthesis of menthol from (±)-citronellal on nickel sulfated zirconia catalysts;Cortes CB;Catal. Today,2011

5. (−)-Menthol biosynthesis and molecular genetics;Croteau RB;Naturwissenschaften,2005

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