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Structure and specificity of a permissive bacterial C-prenyltransferase

Journal Article · · Nature Chemical Biology
 [1];  [2];  [1];  [1];  [1];  [1];  [1];  [2];  [1];  [1]
  1. Univ. of Kentucky, Lexington, KY (United States)
  2. Rice Univ., Houston, TX (United States)
+ Show Author Affiliations
This study highlights the biochemical and structural characterization of the L-tryptophan C6 C-prenyltransferase (C-PT) PriB from Streptomyces sp. RM-5-8. In this work, PriB was found to be uniquely permissive to a diverse array of prenyl donors and acceptors including daptomycin. Two additional PTs also produced novel prenylated daptomycins with improved antibacterial activities over the parent drug.
Research Organization:
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Organization:
Eli Lilly and Company; Merck; National Center for Advancing Translational Sciences (NCATS); National Institutes of Health (NIH); USDOE Office of Science (SC)
Grant/Contract Number:
AC02-06CH11357
OSTI ID:
1356427
Journal Information:
Nature Chemical Biology, Journal Name: Nature Chemical Biology Journal Issue: 4 Vol. 13; ISSN 1552-4450
Publisher:
Nature Publishing GroupCopyright Statement
Country of Publication:
United States
Language:
ENGLISH

References (45)

Potential Rearrangements in the Reaction Catalyzed by the Indole Prenyltransferase FtmPT1 journal September 2013
Structure–Activity Relationship Studies of a Series of Semisynthetic Lipopeptides Leading to the Discovery of Surotomycin, a Novel Cyclic Lipopeptide Being Developed for the Treatment of Clostridium difficile -Associated Diarrhea journal March 2015
Cytotoxic Indolocarbazoles from Actinomadura melliaura ATCC 39691 journal June 2015
Terfestatins B and C, New p -Terphenyl Glycosides Produced by Streptomyces sp. RM-5–8 journal May 2015
Multisite Prenylation of 4-Substituted Tryptophans by Dimethylallyltryptophan Synthase journal January 2013
Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C–H Borylation journal August 2015
Directed Library of Anilinogeranyl Analogues of Farnesyl Diphosphate via Mixed Solid- and Solution-Phase Synthesis journal May 2005
Microtermolides A and B from Termite-Associated Streptomyces sp. and Structural Revision of Vinylamycin journal May 2012
Enzymatic methods for glyco(diversification/randomization) of drugs and small molecules journal January 2011
Mechanistic studies on the indole prenyltransferases journal January 2015
MolProbity : all-atom structure validation for macromolecular crystallography journal December 2009
XDS journal January 2010
Features and development of Coot journal March 2010
The CCP4 suite programs for protein crystallography journal September 1994
Biochemical Characterization of a Novel Indole Prenyltransferase from Streptomyces sp. SN-593 journal March 2010
Biocatalysts for Natural Product Biosynthesis journal June 2014
Evolutionary Relationships of Microbial Aromatic Prenyltransferases journal November 2011
PHENIX: a comprehensive Python-based system for macromolecular structure solution. text January 2010
Enzymatic and chemical modifications of lipopeptide antibiotic A21978C: The synthesis and evaluation of daptomycin (LY146032). journal January 1988
Protein Farnesyltransferase-Catalyzed Isoprenoid Transfer to Peptide Depends on Lipid Size and Shape, not Hydrophobicity journal November 2008
Biochemical Investigations of Two 6-DMATS Enzymes from Streptomyces Reveal New Features of L -Tryptophan Prenyltransferases journal April 2014
Impacts and perspectives of prenyltransferases of the DMATS superfamily for use in biotechnology journal July 2015
Exploring the gas access routes in a [NiFeSe] hydrogenase using crystals pressurized with krypton and oxygen journal August 2020
Tyrosine O -Prenyltransferase SirD Catalyzes S -, C -, and N -Prenylations on Tyrosine and Tryptophan Derivatives journal October 2013
Photoaffinity Analogues of Farnesyl Pyrophosphate Transferable by Protein Farnesyl Transferase journal July 2002
Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products journal June 2005
A new antibiotic kills pathogens without detectable resistance journal January 2015
Protein promiscuity and its implications for biotechnology journal February 2009
A chemocentric view of the natural product inventory journal August 2015
Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution journal September 2007
Manipulation of prenylation reactions by structure-based engineering of bacterial indolactam prenyltransferases journal March 2016
PARP1 exhibits enhanced association and catalytic efficiency with γH2A.X-nucleosome journal December 2019
Cavin1 intrinsically disordered domains are essential for fuzzy electrostatic interactions and caveola formation journal February 2021
Mechanistic studies on the indole prenyltransferases journal January 2015
Boronated tartrolon antibiotic produced by symbiotic cellulose-degrading bacteria in shipworm gills journal January 2013
Daptomycin: From the Mountain to the Clinic, with Essential Help from Francis Tally, MD
  • Eisenstein, Barry I.; Oleson, Jr., Frederick B.; Baltz, Richard H.
  • Clinical Infectious Diseases, Vol. 50, Issue s1 https://doi.org/10.1086/647938
journal January 2010
Geneious Basic: An integrated and extendable desktop software platform for the organization and analysis of sequence data journal April 2012
Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus journal May 2005
MolProbity : all-atom structure validation for macromolecular crystallography journal December 2009
XDS journal January 2010
PHENIX: a comprehensive Python-based system for macromolecular structure solution journal January 2010
Features and development of Coot journal March 2010
Small molecules from the human microbiota journal July 2015
Biochemical Characterization of a Novel Indole Prenyltransferase from Streptomyces sp. SN-593 journal March 2010
Fine-scale population structure and evidence for local adaptation in Australian giant black tiger shrimp (Penaeus monodon) using SNP analysis journal September 2020

Cited By (10)

Eurotiumins A–E, Five New Alkaloids from the Marine-Derived Fungus Eurotium sp. SCSIO F452 journal April 2018
Two Distinct Substrate Binding Modes for the Normal and Reverse Prenylation of Hapalindoles by the Prenyltransferase AmbP3 journal December 2017
Molecular Insight into the Mg 2+ -Dependent Allosteric Control of Indole Prenylation by Aromatic Prenyltransferase AmbP1 journal May 2018
Two Distinct Substrate Binding Modes for the Normal and Reverse Prenylation of Hapalindoles by the Prenyltransferase AmbP3 journal December 2017
Molecular Insight into the Mg 2+ -Dependent Allosteric Control of Indole Prenylation by Aromatic Prenyltransferase AmbP1 journal May 2018
Determination of Alkyl-Donor Promiscuity of Tyrosine- O -Prenyltransferase SirD from Leptosphaeria maculans journal October 2017
Probing the Substrate Promiscuity of Isopentenyl Phosphate Kinase as a Platform for Hemiterpene Analogue Production journal June 2019
Self-association of a highly charged arginine-rich cell-penetrating peptide journal October 2017
A pharmaceutical model for the molecular evolution of microbial natural products journal November 2019
Biocatalysis for terpene-based polymers journal February 2019

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Related Subjects

59 BASIC BIOLOGICAL SCIENCES
Biocatalysis
Biosynthesis
Enzymes
X-ray crystallography