Carba-Sugar Analogs of Glucosamine-6-Phosphate : New Activators for the glmS Riboswitch

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2023
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Gehle, Paul
Esser, Anna
Mayer, Günter
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Riboswitches are 5'-untranslated mRNA regions mostly found in bacteria. They are promising drug targets to overcome emerging bacterial resistances against commonly used antibiotics. The glmS riboswitch is unique among the family of riboswitches as it is a ribozyme that undergoes self-cleavage upon binding to glucosamine-6-phosphate (GlcN6P). Previously, we could show that carba glucosamine-6-phosphate (carba-GlcN6P) induces self-cleavage of the riboswitch with a potency similar to GlcN6P. Here, we report a synthetic approach to a new class of carba-GlcN6P derivatives with an alkoxy substituent in the carba position. Key features of the synthesis are a ring closing metathesis reaction followed by a hydroboration. The strategy gives access to libraries of carba-GlcN6P derivatives. Ribozyme cleavage assays unraveled new activators for the glmS riboswitch from Listeria monocytogenes and Clostridium difficile.

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ISO 690STÄNGLE, David, Bjarne SILKENATH, Paul GEHLE, Anna ESSER, Günter MAYER, Valentin WITTMANN, 2023. Carba-Sugar Analogs of Glucosamine-6-Phosphate : New Activators for the glmS Riboswitch. In: Chemistry - A European Journal. Wiley. 2023, 29(3), e202202378. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.202202378
BibTex
@article{Stangle2023Carba-59142,
  year={2023},
  doi={10.1002/chem.202202378},
  title={Carba-Sugar Analogs of Glucosamine-6-Phosphate : New Activators for the glmS Riboswitch},
  number={3},
  volume={29},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  author={Stängle, David and Silkenath, Bjarne and Gehle, Paul and Esser, Anna and Mayer, Günter and Wittmann, Valentin},
  note={Article Number: e202202378}
}
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