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Title: Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme

Abstract

We present Prodiginines, which are tripyrrole alkaloids displaying a wide array of bioactivities, occur as linear and cyclic congeners. Identification of an unclustered biosynthetic gene led to the discovery of the enzyme responsible for catalyzing the regiospecific C-H activation and cyclization of prodigiosin to cycloprodigiosin in Pseudoalteromonas rubra. This enzyme is related to alkylglycerol monooxygenase and unrelated to RedG, the Rieske oxygenase that produces cyclized prodiginines in Streptomyces, implying convergent evolution.

Authors:
ORCiD logo [1];  [1];  [2];  [1];  [3];  [3];  [3];  [4]; ORCiD logo [3]; ORCiD logo [1];  [5]
+ Show Author Affiliations
  1. Univ. of California, Berkeley, CA (United States). Department of Chemistry
  2. Univ. of California, Berkeley, CA (United States). Department of Chemical and Biomolecular Engineering
  3. DOE Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Biological Systems and Engineering Division
  4. DOE Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Biological Systems and Engineering Division; USDOE Joint Genome Institute (JGI), Walnut Creek, CA (United States)
  5. Univ. of California, Berkeley, CA (United States). Department of Chemical and Biomolecular Engineering and Department of Bioengineering and California Institute for Quantitative Biosciences; DOE Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Biological Systems and Engineering Division; Technical University of Denmark, Horsholm (Denmark). Novo Nordisk Foundation Center for Biosustainability
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1426743
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Nature Chemical Biology
Additional Journal Information:
Journal Volume: 13; Journal Issue: 11; Journal ID: ISSN 1552-4450
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Biosynthesis; Enzymes; Natural products

Citation Formats

de Rond, Tristan, Stow, Parker, Eigl, Ian, Johnson, Rebecca E., Chan, Leanne Jade G., Goyal, Garima, Baidoo, Edward E. K., Hillson, Nathan J., Petzold, Christopher J., Sarpong, Richmond, and Keasling, Jay D. Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme. United States: N. p., 2017. Web. doi:10.1038/nchembio.2471.
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de Rond, Tristan, Stow, Parker, Eigl, Ian, Johnson, Rebecca E., Chan, Leanne Jade G., Goyal, Garima, Baidoo, Edward E. K., Hillson, Nathan J., Petzold, Christopher J., Sarpong, Richmond, & Keasling, Jay D. Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme. United States. https://doi.org/10.1038/nchembio.2471
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de Rond, Tristan, Stow, Parker, Eigl, Ian, Johnson, Rebecca E., Chan, Leanne Jade G., Goyal, Garima, Baidoo, Edward E. K., Hillson, Nathan J., Petzold, Christopher J., Sarpong, Richmond, and Keasling, Jay D. Mon . "Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme". United States. https://doi.org/10.1038/nchembio.2471. https://www.osti.gov/servlets/purl/1426743.
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@article{osti_1426743,
title = {Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme},
author = {de Rond, Tristan and Stow, Parker and Eigl, Ian and Johnson, Rebecca E. and Chan, Leanne Jade G. and Goyal, Garima and Baidoo, Edward E. K. and Hillson, Nathan J. and Petzold, Christopher J. and Sarpong, Richmond and Keasling, Jay D.},
abstractNote = {We present Prodiginines, which are tripyrrole alkaloids displaying a wide array of bioactivities, occur as linear and cyclic congeners. Identification of an unclustered biosynthetic gene led to the discovery of the enzyme responsible for catalyzing the regiospecific C-H activation and cyclization of prodigiosin to cycloprodigiosin in Pseudoalteromonas rubra. This enzyme is related to alkylglycerol monooxygenase and unrelated to RedG, the Rieske oxygenase that produces cyclized prodiginines in Streptomyces, implying convergent evolution.},
doi = {10.1038/nchembio.2471},
journal = {Nature Chemical Biology},
number = 11,
volume = 13,
place = {United States},
year = {Mon Sep 11 00:00:00 EDT 2017},
month = {Mon Sep 11 00:00:00 EDT 2017}
}
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https://doi.org/10.1038/nchembio.2471
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Elucidation of Final Steps of the Marineosins Biosynthetic Pathway through Identification and Characterization of the Corresponding Gene Cluster
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Antimalarial Activity of Natural and Synthetic Prodiginines
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Stereospecific Synthesis of 23-Hydroxyundecylprodiginines and Analogues and Conversion to Antimalarial Premarineosins via a Rieske Oxygenase Catalyzed Bicyclization
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Identification of a prodigiosin cyclization gene in the roseophilin producer and production of a new cyclized prodigiosin in a heterologous host
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The biosynthesis and regulation of bacterial prodiginines
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Anticancer and immunosuppressive properties of bacterial prodiginines
journal, December 2007

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  • Future Microbiology, Vol. 2, Issue 6
  • DOI: 10.2217/17460913.2.6.605
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    ( R )‐Metacycloprodigiosin‐HCl: Chiroptical properties and structure
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    Biosynthesis and Bioactivity of Prodiginine Analogs in Marine Bacteria, Pseudoalteromonas: A Mini Review
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    • Sakai-Kawada, Francis E.; Ip, Courtney G.; Hagiwara, Kehau A.
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