Alkyne-Functionalized Coumarin Compound for Analytic and Preparative 4-Thiouridine Labeling

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Katharina Schmid
  • Maria Adobes-Vidal
  • Mark Helm
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000399965800032&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1021/acs.bioconjchem.7b00035
Externe Identifier
  • Clarivate Analytics Document Solution ID: ET0PL
  • PubMed Identifier: 28263563
ISSN
1043-1802
Ausgabe der Veröffentlichung
4
Zeitschrift
BIOCONJUGATE CHEMISTRY
Paginierung
1123 - 1134
Datum der Veröffentlichung
2017
Status
Published
Titel
Alkyne-Functionalized Coumarin Compound for Analytic and Preparative 4-Thiouridine Labeling
Sub types
  • Article
Ausgabe der Zeitschrift
28

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Autoren
  • Katharina Schmid
  • Maria Adobes-Vidal
  • Mark Helm
DOI
10.1021/acs.bioconjchem.7b00035
eISSN
1520-4812
ISSN
1043-1802
Ausgabe der Veröffentlichung
4
Zeitschrift
Bioconjugate Chemistry
Sprache
en
Online publication date
2017
Paginierung
1123 - 1134
Datum der Veröffentlichung
2017
Status
Published
Herausgeber
American Chemical Society (ACS)
Herausgeber URL
http://dx.doi.org/10.1021/acs.bioconjchem.7b00035
Datum der Datenerfassung
2023
Titel
Alkyne-Functionalized Coumarin Compound for Analytic and Preparative 4-Thiouridine Labeling
Ausgabe der Zeitschrift
28

Datenquelle: Crossref

Abstract
Bioconjugation of RNA is a dynamic field recently reinvigorated by a surge in research on post-transcriptional modification. This work focuses on the bioconjugation of 4-thiouridine, a nucleoside that occurs as a post-transcriptional modification in bacterial RNA and is used as a metabolic label and for cross-linking purposes in eukaryotic RNA. A newly designed coumarin compound named 4-bromomethyl-7-propargyloxycoumarin (PBC) is introduced, which exhibits remarkable selectivity for 4-thiouridine. Bearing a terminal alkyne group, it is conductive to secondary bioconjugation via "click chemistry", thereby offering a wide range of preparative and analytical options. We applied PBC to quantitatively monitor the metabolic incorporation of s<sup>4</sup>U as a label into RNA and for site-specific introduction of a fluorophore into bacterial tRNA at position 8, allowing the determination of its binding constant to an RNA-modification enzyme.
Addresses
  • Institute of Pharmacy and Biochemistry, Johannes-Gutenberg University Mainz , Staudingerweg 5, D-55128 Mainz, Germany.
Autoren
  • Katharina Schmid
  • Maria Adobes-Vidal
  • Mark Helm
DOI
10.1021/acs.bioconjchem.7b00035
eISSN
1520-4812
Externe Identifier
  • PubMed Identifier: 28263563
Funding acknowledgements
  • Deutsche Forschungsgemeinschaft: HE3397/9-1
Open access
false
ISSN
1043-1802
Ausgabe der Veröffentlichung
4
Zeitschrift
Bioconjugate chemistry
Schlüsselwörter
  • Alkynes
  • Coumarins
  • RNA, Bacterial
  • Thiouridine
  • Affinity Labels
  • Staining and Labeling
  • RNA Processing, Post-Transcriptional
  • Binding Sites
  • Protein Binding
  • Click Chemistry
Sprache
eng
Medium
Print-Electronic
Online publication date
2017
Paginierung
1123 - 1134
Datum der Veröffentlichung
2017
Status
Published
Datum der Datenerfassung
2017
Titel
Alkyne-Functionalized Coumarin Compound for Analytic and Preparative 4-Thiouridine Labeling.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
28

Datenquelle: Europe PubMed Central

Abstract
Bioconjugation of RNA is a dynamic field recently reinvigorated by a surge in research on post-transcriptional modification. This work focuses on the bioconjugation of 4-thiouridine, a nucleoside that occurs as a post-transcriptional modification in bacterial RNA and is used as a metabolic label and for cross-linking purposes in eukaryotic RNA. A newly designed coumarin compound named 4-bromomethyl-7-propargyloxycoumarin (PBC) is introduced, which exhibits remarkable selectivity for 4-thiouridine. Bearing a terminal alkyne group, it is conductive to secondary bioconjugation via "click chemistry", thereby offering a wide range of preparative and analytical options. We applied PBC to quantitatively monitor the metabolic incorporation of s4U as a label into RNA and for site-specific introduction of a fluorophore into bacterial tRNA at position 8, allowing the determination of its binding constant to an RNA-modification enzyme.
Autoren
  • Katharina Schmid
  • Maria Adobes-Vidal
  • Mark Helm
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/28263563
DOI
10.1021/acs.bioconjchem.7b00035
eISSN
1520-4812
Ausgabe der Veröffentlichung
4
Zeitschrift
Bioconjug Chem
Schlüsselwörter
  • Affinity Labels
  • Alkynes
  • Binding Sites
  • Click Chemistry
  • Coumarins
  • Protein Binding
  • RNA Processing, Post-Transcriptional
  • RNA, Bacterial
  • Staining and Labeling
  • Thiouridine
Sprache
eng
Country
United States
Paginierung
1123 - 1134
Datum der Veröffentlichung
2017
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2017
Titel
Alkyne-Functionalized Coumarin Compound for Analytic and Preparative 4-Thiouridine Labeling.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
28

Datenquelle: PubMed

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