Literature DB >> 21999343

Imaging mass spectrometry and genome mining via short sequence tagging identified the anti-infective agent arylomycin in Streptomyces roseosporus.

Wei-Ting Liu1, Roland D Kersten, Yu-Liang Yang, Bradley S Moore, Pieter C Dorrestein.   

Abstract

Here, we described the discovery of anti-infective agent arylomycin and its biosynthetic gene cluster in an industrial daptomycin producing strain Streptomyces roseosporus. This was accomplished via the use of MALDI imaging mass spectrometry (IMS) along with peptidogenomic approach in which we have expanded to short sequence tagging (SST) described herein. Using IMS, we observed that prior to the production of daptomycin, a cluster of ions (1-3) was produced by S. roseosporus and correlated well with the decreased staphylococcal cell growth. With a further adopted SST peptidogenomics approach, which relies on the generation of sequence tags from tandem mass spectrometric data and query against genomes to identify the biosynthetic genes, we were able to identify these three molecules (1-3) to arylomycins, a class of broad-spectrum antibiotics that target type I signal peptidase. The gene cluster was then identified. This highlights the strength of IMS and MS guided genome mining approaches in effectively bridging the gap between phenotypes, chemotypes, and genotypes.

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Year:  2011        PMID: 21999343      PMCID: PMC3251218          DOI: 10.1021/ja2040877

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  40 in total

1.  Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains.

Authors:  G L Challis; J Ravel; C A Townsend
Journal:  Chem Biol       Date:  2000-03

2.  The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases.

Authors:  T Stachelhaus; H D Mootz; M A Marahiel
Journal:  Chem Biol       Date:  1999-08

3.  Novel lipoglycopeptides as inhibitors of bacterial signal peptidase I.

Authors:  Palaniappan Kulanthaivel; Adam J Kreuzman; Mark A Strege; Matthew D Belvo; Tim A Smitka; Matthew Clemens; James R Swartling; Kristina L Minton; Feng Zheng; Eddie L Angleton; Deborah Mullen; Louis N Jungheim; Valentine J Klimkowski; Thalia I Nicas; Richard C Thompson; Sheng-Bin Peng
Journal:  J Biol Chem       Date:  2004-06-01       Impact factor: 5.157

4.  Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic.

Authors:  A M van Wageningen; P N Kirkpatrick; D H Williams; B R Harris; J K Kershaw; N J Lennard; M Jones; S J Jones; P J Solenberg
Journal:  Chem Biol       Date:  1998-03

5.  Daptomycin biosynthesis in Streptomyces roseosporus: cloning and analysis of the gene cluster and revision of peptide stereochemistry.

Authors:  Vivian Miao; Marie-Françoise Coëffet-Legal; Paul Brian; Renee Brost; Julia Penn; Andrew Whiting; Steven Martin; Robert Ford; Ian Parr; Mario Bouchard; Christopher J Silva; Stephen K Wrigley; Richard H Baltz
Journal:  Microbiology       Date:  2005-05       Impact factor: 2.777

6.  Crystal structure of OxyC, a cytochrome P450 implicated in an oxidative C-C coupling reaction during vancomycin biosynthesis.

Authors:  Olena Pylypenko; Francesca Vitali; Katja Zerbe; John A Robinson; Ilme Schlichting
Journal:  J Biol Chem       Date:  2003-07-29       Impact factor: 5.157

7.  Crystallographic and biophysical analysis of a bacterial signal peptidase in complex with a lipopeptide-based inhibitor.

Authors:  Mark Paetzel; Jonathon J Goodall; Malgosia Kania; Ross E Dalbey; Malcolm G P Page
Journal:  J Biol Chem       Date:  2004-05-10       Impact factor: 5.157

Review 8.  Penicillin and cephalosporin biosynthetic genes: structure, organization, regulation, and evolution.

Authors:  Y Aharonowitz; G Cohen; J F Martin
Journal:  Annu Rev Microbiol       Date:  1992       Impact factor: 15.500

9.  Arylomycins A and B, new biaryl-bridged lipopeptide antibiotics produced by Streptomyces sp. Tü 6075. II. Structure elucidation.

Authors:  Alexandra Höltzel; Dietmar G Schmid; Graeme J Nicholson; Stefan Stevanovic; Judith Schimana; Klaus Gebhardt; Hans-Peter Fiedler; Günther Jung
Journal:  J Antibiot (Tokyo)       Date:  2002-06       Impact factor: 2.649

10.  A mass spectrometry-guided genome mining approach for natural product peptidogenomics.

Authors:  Roland D Kersten; Yu-Liang Yang; Yuquan Xu; Peter Cimermancic; Sang-Jip Nam; William Fenical; Michael A Fischbach; Bradley S Moore; Pieter C Dorrestein
Journal:  Nat Chem Biol       Date:  2011-10-09       Impact factor: 15.040

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  27 in total

1.  Observing the invisible through imaging mass spectrometry, a window into the metabolic exchange patterns of microbes.

Authors:  David J Gonzalez; Yuquan Xu; Yu-Liang Yang; Eduardo Esquenazi; Wei-Ting Liu; Anna Edlund; Tram Duong; Liangcheng Du; István Molnár; William H Gerwick; Paul R Jensen; Michael Fischbach; Chih-Chuang Liaw; Paul Straight; Victor Nizet; Pieter C Dorrestein
Journal:  J Proteomics       Date:  2012-05-26       Impact factor: 4.044

Review 2.  Genetic manipulation of secondary metabolite biosynthesis for improved production in Streptomyces and other actinomycetes.

Authors:  Richard H Baltz
Journal:  J Ind Microbiol Biotechnol       Date:  2015-09-12       Impact factor: 3.346

Review 3.  Prospecting genomes for lasso peptides.

Authors:  Mikhail O Maksimov; A James Link
Journal:  J Ind Microbiol Biotechnol       Date:  2013-10-19       Impact factor: 3.346

Review 4.  Actinomycetes biosynthetic potential: how to bridge in silico and in vivo?

Authors:  Yuriy Rebets; Elke Brötz; Bogdan Tokovenko; Andriy Luzhetskyy
Journal:  J Ind Microbiol Biotechnol       Date:  2013-10-15       Impact factor: 3.346

5.  MbtH homology codes to identify gifted microbes for genome mining.

Authors:  Richard H Baltz
Journal:  J Ind Microbiol Biotechnol       Date:  2013-11-07       Impact factor: 3.346

Review 6.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

Review 7.  Insights into microbial cryptic gene activation and strain improvement: principle, application and technical aspects.

Authors:  Kozo Ochi
Journal:  J Antibiot (Tokyo)       Date:  2016-07-06       Impact factor: 2.649

Review 8.  Mass spectrometry tools and workflows for revealing microbial chemistry.

Authors:  Tal Luzzatto-Knaan; Alexey V Melnik; Pieter C Dorrestein
Journal:  Analyst       Date:  2015-08-07       Impact factor: 4.616

Review 9.  Genome Mining as New Challenge in Natural Products Discovery.

Authors:  Luisa Albarano; Roberta Esposito; Nadia Ruocco; Maria Costantini
Journal:  Mar Drugs       Date:  2020-04-09       Impact factor: 5.118

10.  Biosynthesis of Strained Piperazine Alkaloids: Uncovering the Concise Pathway of Herquline A.

Authors:  Xia Yu; Fang Liu; Yi Zou; Man-Cheng Tang; Leibniz Hang; K N Houk; Yi Tang
Journal:  J Am Chem Soc       Date:  2016-10-06       Impact factor: 15.419

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