Literature DB >> 24151049

Minimum set of cytochromes P450 for reconstituting the biosynthesis of camalexin, a major Arabidopsis antibiotic.

Andrew P Klein1, Gülbenk Anarat-Cappillino, Elizabeth S Sattely.   

Abstract

Bringing it all together: The missing key step in the biosynthesis of camalexin was uncovered by in vitro biochemical characterization. The coupling of Trp- and Cys-derived fragments through CS bond formation is promoted by an unusual cytochrome P450 CYP71A13. The in vitro reconstitution of the camalexin biosynthesis (left) from Trp and Cys was achieved using just three cytochromes P450. IAN=indole-3-acetonitrile.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CS bond formation; biosynthesis; camalexin; cytochromes; natural products

Mesh:

Substances:

Year:  2013        PMID: 24151049      PMCID: PMC3867539          DOI: 10.1002/anie.201307454

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  15 in total

Review 1.  Unusual P450 reactions in plant secondary metabolism.

Authors:  Masaharu Mizutani; Fumihiko Sato
Journal:  Arch Biochem Biophys       Date:  2010-10-25       Impact factor: 4.013

2.  The multifunctional enzyme CYP71B15 (PHYTOALEXIN DEFICIENT3) converts cysteine-indole-3-acetonitrile to camalexin in the indole-3-acetonitrile metabolic network of Arabidopsis thaliana.

Authors:  Christoph Böttcher; Lore Westphal; Constanze Schmotz; Elke Prade; Dierk Scheel; Erich Glawischnig
Journal:  Plant Cell       Date:  2009-06-30       Impact factor: 11.277

3.  Innate immune responses activated in Arabidopsis roots by microbe-associated molecular patterns.

Authors:  Yves A Millet; Cristian H Danna; Nicole K Clay; Wisuwat Songnuan; Matthew D Simon; Danièle Werck-Reichhart; Frederick M Ausubel
Journal:  Plant Cell       Date:  2010-03-26       Impact factor: 11.277

4.  Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin.

Authors:  S Bak; R A Kahn; H L Nielsen; B L Moller; B A Halkier
Journal:  Plant Mol Biol       Date:  1998-02       Impact factor: 4.076

5.  Glutathione-indole-3-acetonitrile is required for camalexin biosynthesis in Arabidopsis thaliana.

Authors:  Tongbing Su; Juan Xu; Yuan Li; Lei Lei; Luo Zhao; Hailian Yang; Jidong Feng; Guoqin Liu; Dongtao Ren
Journal:  Plant Cell       Date:  2011-01-14       Impact factor: 11.277

6.  A dedicated glutathione S-transferase mediates carbon-sulfur bond formation in gliotoxin biosynthesis.

Authors:  Daniel H Scharf; Nicole Remme; Andreas Habel; Pranatchareeya Chankhamjon; Kirstin Scherlach; Thorsten Heinekamp; Peter Hortschansky; Axel A Brakhage; Christian Hertweck
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

7.  CYP83b1 is the oxime-metabolizing enzyme in the glucosinolate pathway in Arabidopsis.

Authors:  C H Hansen; L Du; P Naur; C E Olsen; K B Axelsen; A J Hick; J A Pickett; B A Halkier
Journal:  J Biol Chem       Date:  2001-05-01       Impact factor: 5.157

8.  Increased intracellular H₂O₂ availability preferentially drives glutathione accumulation in vacuoles and chloroplasts.

Authors:  Guillaume Queval; Danielle Jaillard; Bernd Zechmann; Graham Noctor
Journal:  Plant Cell Environ       Date:  2010-10-04       Impact factor: 7.228

9.  Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis.

Authors:  Majse Nafisi; Sameer Goregaoker; Christopher J Botanga; Erich Glawischnig; Carl E Olsen; Barbara A Halkier; Jane Glazebrook
Journal:  Plant Cell       Date:  2007-06-15       Impact factor: 11.277

10.  Metabolon formation in dhurrin biosynthesis.

Authors:  Kirsten Annette Nielsen; David B Tattersall; Patrik Raymond Jones; Birger Lindberg Møller
Journal:  Phytochemistry       Date:  2007-08-15       Impact factor: 4.072

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  18 in total

1.  A chemocentric view of the natural product inventory.

Authors:  Christopher T Walsh
Journal:  Nat Chem Biol       Date:  2015-09       Impact factor: 15.040

2.  Biosynthesis of cabbage phytoalexins from indole glucosinolate.

Authors:  Andrew P Klein; Elizabeth S Sattely
Journal:  Proc Natl Acad Sci U S A       Date:  2017-02-02       Impact factor: 11.205

3.  Plant-derived coumarins shape the composition of an Arabidopsis synthetic root microbiome.

Authors:  Mathias J E E E Voges; Yang Bai; Paul Schulze-Lefert; Elizabeth S Sattely
Journal:  Proc Natl Acad Sci U S A       Date:  2019-05-31       Impact factor: 11.205

4.  The Formation of a Camalexin Biosynthetic Metabolon.

Authors:  Stefanie Mucha; Stephanie Heinzlmeir; Verena Kriechbaumer; Benjamin Strickland; Charlotte Kirchhelle; Manisha Choudhary; Natalie Kowalski; Ruth Eichmann; Ralph Hückelhoven; Erwin Grill; Bernhard Kuster; Erich Glawischnig
Journal:  Plant Cell       Date:  2019-09-11       Impact factor: 11.277

5.  In Vitro Reconstitution of Metabolic Pathways: Insights into Nature's Chemical Logic.

Authors:  Brian Lowry; Christopher T Walsh; Chaitan Khosla
Journal:  Synlett       Date:  2015       Impact factor: 2.454

6.  TRANSCRIPTION ACTIVATOR-LIKE EFFECTOR NUCLEASE-Mediated Generation and Metabolic Analysis of Camalexin-Deficient cyp71a12 cyp71a13 Double Knockout Lines.

Authors:  Teresa M Müller; Christoph Böttcher; Robert Morbitzer; Cornelia C Götz; Johannes Lehmann; Thomas Lahaye; Erich Glawischnig
Journal:  Plant Physiol       Date:  2015-05-07       Impact factor: 8.340

7.  The Biosynthetic Pathway of Indole-3-Carbaldehyde and Indole-3-Carboxylic Acid Derivatives in Arabidopsis.

Authors:  Christoph Böttcher; Alexandra Chapman; Franziska Fellermeier; Manisha Choudhary; Dierk Scheel; Erich Glawischnig
Journal:  Plant Physiol       Date:  2014-04-11       Impact factor: 8.340

8.  The chemical logic of plant natural product biosynthesis.

Authors:  Gülbenk Anarat-Cappillino; Elizabeth S Sattely
Journal:  Curr Opin Plant Biol       Date:  2014-04-14       Impact factor: 7.834

Review 9.  Computational genomic identification and functional reconstitution of plant natural product biosynthetic pathways.

Authors:  Marnix H Medema; Anne Osbourn
Journal:  Nat Prod Rep       Date:  2016-06-20       Impact factor: 13.423

10.  Two cytochromes P450 catalyze S-heterocyclizations in cabbage phytoalexin biosynthesis.

Authors:  Andrew P Klein; Elizabeth S Sattely
Journal:  Nat Chem Biol       Date:  2015-09-21       Impact factor: 15.040

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