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Literature DB >> 21486059

Carba-sugars activate the glmS-riboswitch of Staphylococcus aureus.

Christina E Lünse, Magnus S Schmidt, Valentin Wittmann, Günter Mayer.

Abstract

The glmS-riboswitch is unique among riboswitch families as it represents a metabolite-dependent ribozyme that undergoes self-cleavage upon recognition of glucosamin-6-phosphate. The glmS-riboswitch is located in the 5'-untranslated region of bacterial genes involved in cell wall biosynthesis. Therefore, this riboswitch represents a promising target for developing new antibiotics. We describe the metabolite-dependent glmS-riboswitch of pathologically relevant and vancomycin-resistant Staphylococcus aureus and the discovery and synthesis of a carba-sugar with potency similar to that of the native metabolite glucosamine-6-phosphate in modulating riboswitch activity. This compound represents a valuable lead structure for the development of antibiotics with a novel mode of action.

Entities: Chemical Species

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Year: 2011 PMID： 21486059 DOI： 10.1021/cb200016d

Source DB: PubMed Journal: ACS Chem Biol ISSN： 1554-8929 Impact factor: 5.100

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Cited

18 in total

1. Identification of ligand analogues that control c-di-GMP riboswitches.

Authors: Kazuhiro Furukawa; Hongzhou Gu; Narasimhan Sudarsan; Yoshihiro Hayakawa; Mamoru Hyodo; Ronald R Breaker
Journal: ACS Chem Biol Date: 2012-06-19 Impact factor: 5.100

2. Mechanism and distribution of glmS ribozymes.

Authors: Phillip J McCown; Wade C Winkler; Ronald R Breaker
Journal: Methods Mol Biol Date: 2012

Review 3. Using Genome Sequence to Enable the Design of Medicines and Chemical Probes.

Authors: Alicia J Angelbello; Jonathan L Chen; Jessica L Childs-Disney; Peiyuan Zhang; Zi-Fu Wang; Matthew D Disney
Journal: Chem Rev Date: 2018-01-11 Impact factor: 60.622

4. Novel riboswitch-binding flavin analog that protects mice against Clostridium difficile infection without inhibiting cecal flora.

Authors: Kenneth F Blount; Cynthia Megyola; Mark Plummer; David Osterman; Tim O'Connell; Paul Aristoff; Cheryl Quinn; R Alan Chrusciel; Toni J Poel; Heinrich J Schostarez; Catherine A Stewart; Daniel P Walker; Peter G M Wuts; Ronald R Breaker
Journal: Antimicrob Agents Chemother Date: 2015-07-13 Impact factor: 5.191

10. Stereospecific synthesis of methyl 2-amino-2,4-dideoxy-6S-deuterio-α-D-xylo-hexopyranoside and methyl 2-amino-2,4-dideoxy-6S-deuterio-4-propyl-α-d-glucopyranoside: Side chain conformation of the novel aminoglycoside antibiotic propylamycin.

Authors: Michael G Pirrone; Takahiko Matsushita; Andrea Vasella; David Crich
Journal: Carbohydr Res Date: 2020-03-16 Impact factor: 2.104

Carba-sugars activate the glmS-riboswitch of Staphylococcus aureus.

1. Identification of ligand analogues that control c-di-GMP riboswitches.

2. Mechanism and distribution of glmS ribozymes.

Review 3. Using Genome Sequence to Enable the Design of Medicines and Chemical Probes.

4. Novel riboswitch-binding flavin analog that protects mice against Clostridium difficile infection without inhibiting cecal flora.

5. Engineered allosteric ribozymes that sense the bacterial second messenger cyclic diguanosyl 5'-monophosphate.

6. In vitro selection of allosteric ribozymes that sense the bacterial second messenger c-di-GMP.

7. The glmS ribozyme cofactor is a general acid-base catalyst.

8. Parallel Discovery Strategies Provide a Basis for Riboswitch Ligand Design.

9. Glucosamine and glucosamine-6-phosphate derivatives: catalytic cofactor analogues for the glmS ribozyme.

10. Stereospecific synthesis of methyl 2-amino-2,4-dideoxy-6S-deuterio-α-D-xylo-hexopyranoside and methyl 2-amino-2,4-dideoxy-6S-deuterio-4-propyl-α-d-glucopyranoside: Side chain conformation of the novel aminoglycoside antibiotic propylamycin.