A Vastly Increased Chemical Variety of RNA Modifications Containing a Thioacetal Structure

Publication type:
Journal article
Metadata:
Autoren
  • Christina Dal Magro
  • Patrick Keller
  • Annika Kotter
  • Stephan Werner
  • Victor Duarte
  • Virginie Marchand
  • Michael Ignarski
  • Anja Freiwald
  • Roman-Ulrich Mueller
  • Christoph Dieterich
  • Yuri Motorin
  • Falk Butter
  • Mohamed Atta
  • Mark Helm
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000435766800057&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/anie.201713188
eISSN
1521-3773
Externe Identifier
  • Clarivate Analytics Document Solution ID: GK0AA
  • PubMed Identifier: 29624844
ISSN
1433-7851
Ausgabe der Veröffentlichung
26
Zeitschrift
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Schlüsselwörter
  • LC-MS
  • radical-SAM enzymes
  • RNA modifications
  • isotope labelling
  • thioacetals
Paginierung
7893 - 7897
Datum der Veröffentlichung
2018
Status
Published
Titel
A Vastly Increased Chemical Variety of RNA Modifications Containing a Thioacetal Structure
Sub types
  • Article
Ausgabe der Zeitschrift
57

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<jats:title>Abstract</jats:title><jats:p>Recently discovered new chemical entities in RNA modifications have involved surprising functional groups that enlarge the chemical space of RNA. Using LC‐MS, we found over 100 signals of RNA constituents that contained a ribose moiety in tRNAs from <jats:italic>E. coli</jats:italic>. Feeding experiments with variegated stable isotope labeled compounds identified 37 compounds that are new structures of RNA modifications. One structure was elucidated by deuterium exchange and high‐resolution mass spectrometry. The structure of msms<jats:sup>2</jats:sup>i<jats:sup>6</jats:sup>A (2‐methylthiomethylenethio‐N6‐isopentenyl‐adenosine) was confirmed by methione‐D3 feeding experiments and by synthesis of the nucleobase. The msms<jats:sup>2</jats:sup>i<jats:sup>6</jats:sup>A contains a thioacetal, shown in vitro to be biosynthetically derived from ms<jats:sup>2</jats:sup>i<jats:sup>6</jats:sup>A by the radical‐SAM enzyme MiaB. This enzyme performs thiomethylation, forming ms<jats:sup>2</jats:sup>i<jats:sup>6</jats:sup>A from i<jats:sup>6</jats:sup>A in a first turnover. The new thioacetal is formed by a second turnover. Along with the pool of 36 new modifications, this work describes a new layer of RNA modification chemistry.</jats:p>
Autoren
  • Christina Dal Magro
  • Patrick Keller
  • Annika Kotter
  • Stephan Werner
  • Victor Duarte
  • Virginie Marchand
  • Michael Ignarski
  • Anja Freiwald
  • Roman‐Ulrich Müller
  • Christoph Dieterich
  • Yuri Motorin
  • Falk Butter
  • Mohamed Atta
  • Mark Helm
DOI
10.1002/anie.201713188
eISSN
1521-3773
ISSN
1433-7851
Ausgabe der Veröffentlichung
26
Zeitschrift
Angewandte Chemie International Edition
Sprache
en
Online publication date
2018
Paginierung
7893 - 7897
Datum der Veröffentlichung
2018
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/anie.201713188
Datum der Datenerfassung
2023
Titel
A Vastly Increased Chemical Variety of RNA Modifications Containing a Thioacetal Structure
Ausgabe der Zeitschrift
57

Data source: Crossref

Abstract
Recently discovered new chemical entities in RNA modifications have involved surprising functional groups that enlarge the chemical space of RNA. Using LC-MS, we found over 100 signals of RNA constituents that contained a ribose moiety in tRNAs from E. coli. Feeding experiments with variegated stable isotope labeled compounds identified 37 compounds that are new structures of RNA modifications. One structure was elucidated by deuterium exchange and high-resolution mass spectrometry. The structure of msms<sup>2</sup> i<sup>6</sup> A (2-methylthiomethylenethio-N6-isopentenyl-adenosine) was confirmed by methione-D3 feeding experiments and by synthesis of the nucleobase. The msms<sup>2</sup> i<sup>6</sup> A contains a thioacetal, shown in vitro to be biosynthetically derived from ms<sup>2</sup> i<sup>6</sup> A by the radical-SAM enzyme MiaB. This enzyme performs thiomethylation, forming ms<sup>2</sup> i<sup>6</sup> A from i<sup>6</sup> A in a first turnover. The new thioacetal is formed by a second turnover. Along with the pool of 36 new modifications, this work describes a new layer of RNA modification chemistry.
Addresses
  • Institute of Pharmacy and Biochemistry, Johannes Gutenberg-University Mainz, Staudingerweg 5, 55128, Mainz, Germany.
Autoren
  • Christina Dal Magro
  • Patrick Keller
  • Annika Kotter
  • Stephan Werner
  • Victor Duarte
  • Virginie Marchand
  • Michael Ignarski
  • Anja Freiwald
  • Roman-Ulrich Müller
  • Christoph Dieterich
  • Yuri Motorin
  • Falk Butter
  • Mohamed Atta
  • Mark Helm
DOI
10.1002/anie.201713188
eISSN
1521-3773
Externe Identifier
  • PubMed Identifier: 29624844
Funding acknowledgements
  • Deutsche Forschungsgemeinschaft: SPP 1784
  • Deutsche Forschungsgemeinschaft: HE 3397-13/1
  • Deutsche Forschungsgemeinschaft: HE 3397-14/1
Open access
false
ISSN
1433-7851
Ausgabe der Veröffentlichung
26
Zeitschrift
Angewandte Chemie (International ed. in English)
Schlüsselwörter
  • Escherichia coli
  • Acetals
  • Sulfhydryl Compounds
  • RNA, Bacterial
  • Chromatography, Liquid
  • Nucleic Acid Conformation
  • Tandem Mass Spectrometry
Sprache
eng
Medium
Print-Electronic
Online publication date
2018
Paginierung
7893 - 7897
Datum der Veröffentlichung
2018
Status
Published
Datum der Datenerfassung
2018
Titel
A Vastly Increased Chemical Variety of RNA Modifications Containing a Thioacetal Structure.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
57

Data source: Europe PubMed Central

Abstract
Recently discovered new chemical entities in RNA modifications have involved surprising functional groups that enlarge the chemical space of RNA. Using LC-MS, we found over 100 signals of RNA constituents that contained a ribose moiety in tRNAs from E. coli. Feeding experiments with variegated stable isotope labeled compounds identified 37 compounds that are new structures of RNA modifications. One structure was elucidated by deuterium exchange and high-resolution mass spectrometry. The structure of msms2 i6 A (2-methylthiomethylenethio-N6-isopentenyl-adenosine) was confirmed by methione-D3 feeding experiments and by synthesis of the nucleobase. The msms2 i6 A contains a thioacetal, shown in vitro to be biosynthetically derived from ms2 i6 A by the radical-SAM enzyme MiaB. This enzyme performs thiomethylation, forming ms2 i6 A from i6 A in a first turnover. The new thioacetal is formed by a second turnover. Along with the pool of 36 new modifications, this work describes a new layer of RNA modification chemistry.
Autoren
  • Christina Dal Magro
  • Patrick Keller
  • Annika Kotter
  • Stephan Werner
  • Victor Duarte
  • Virginie Marchand
  • Michael Ignarski
  • Anja Freiwald
  • Roman-Ulrich Müller
  • Christoph Dieterich
  • Yuri Motorin
  • Falk Butter
  • Mohamed Atta
  • Mark Helm
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/29624844
DOI
10.1002/anie.201713188
eISSN
1521-3773
Ausgabe der Veröffentlichung
26
Zeitschrift
Angew Chem Int Ed Engl
Schlüsselwörter
  • LC-MS
  • RNA modifications
  • isotope labelling
  • radical-SAM enzymes
  • thioacetals
  • Acetals
  • Chromatography, Liquid
  • Escherichia coli
  • Nucleic Acid Conformation
  • RNA, Bacterial
  • Sulfhydryl Compounds
  • Tandem Mass Spectrometry
Sprache
eng
Country
Germany
Paginierung
7893 - 7897
Datum der Veröffentlichung
2018
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2019
Titel
A Vastly Increased Chemical Variety of RNA Modifications Containing a Thioacetal Structure.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
57

Data source: PubMed

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