ArticleBiochemistry2011
glmS Riboswitch binding to the glucosamine-6-phosphate α-anomer shifts the pKa toward neutrality.
Article in Biochemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 41 citations in OpenAlex.
- Phosphonate and Thiasugar Analogues of Glucosamine-6-phosphate: Activation of theACS chemical biology · 2023Article
- Carba-Sugar Analogs of Glucosamine-6-Phosphate: New Activators for the glmS Riboswitch.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Self-cleaving ribozymes: substrate specificity and synthetic biology applications.RSC chemical biology · 2021Review
- Exploring the Druggability of Conserved RNA Regulatory Elements in the SARS-CoV-2 Genome.Angewandte Chemie (International ed. in English) · 2021Article
- Riboswitch Mechanisms: New Tricks for an Old Dog.Biochemistry. Biokhimiia · 2021Review
- Small RNA-binding protein RapZ mediates cell envelope precursor sensing and signaling in Escherichia coli.The EMBO journal · 2020Article
- Ligand-observed NMR techniques to probe RNA-small molecule interactions.Methods in enzymology · 2019Article
- A Long-Lived Halogen-Bonding Anion Triple Helicate Accommodates Rapid Guest Exchange.Angewandte Chemie (International ed. in English) · 2018Article
- Recent advances and future trends of riboswitches: attractive regulatory tools.World journal of microbiology & biotechnology · 2018Review
- Elucidation of Catalytic Strategies of Small Nucleolytic Ribozymes From Comparative Analysis of Active Sites.ACS catalysis · 2018Article
- Many Activities, One Structure: Functional Plasticity of Ribozyme Folds.Molecules (Basel, Switzerland) · 2016Review
- In vitro evolution of coenzyme-independent variants from the glmS ribozyme structural scaffold.Methods (San Diego, Calif.) · 2016Article
- Chemical feasibility of the general acid/base mechanism of glmS ribozyme self-cleavage.Biopolymers · 2015Article
- Role of the active site guanine in the glmS ribozyme self-cleavage mechanism: quantum mechanical/molecular mechanical free energy simulations.Journal of the American Chemical Society · 2015Article
- An Efficient Minimum Free Energy Structure-Based Search Method for Riboswitch Identification Based on Inverse RNA Folding.PloS one · 2015Article
- Role of tautomerism in RNA biochemistry.RNA (New York, N.Y.) · 2015Review
- Phosphatase-inert glucosamine 6-phosphate mimics serve as actuators of the glmS riboswitch.ACS chemical biology · 2014Article
- Nucleic acid catalysis: metals, nucleobases, and other cofactors.Chemical reviews · 2014Review
- An in vitro evolved glmS ribozyme has the wild-type fold but loses coenzyme dependence.Nature chemical biology · 2013Article
- Glucosamine and glucosamine-6-phosphate derivatives: catalytic cofactor analogues for the glmS ribozyme.The Journal of organic chemistry · 2013Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The glmS riboswitch regulates gene expression through a self-cleavage activity. The reaction is catalyzed with the assistance of the metabolite cofactor glucosamine-6-phosphate (GlcN6P), whose amino group is proposed to serve as the general acid during the reaction. This reaction is pH-dependent with a pK(a) that is lower than the observed pK(a) for the amine of GlcN6P in solution. GlcN6P, like other pyranose sugars, undergoes spontaneous and rapid interconversion between the α and β anomers at the C1 position. Here we demonstrate by NMR that the Bacillus anthracis glmS riboswitch selectively binds the α-anomer of GlcN6P with a maximum binding affinity of 0.36 mM and that binding is pH-dependent. We also report that the anomeric ratio between α and β is pH-dependent and the pK(a)s of the two amines differ by 0.5 pH units, α being the higher of the two (pK(a)=8.3). The pH dependence of binding reveals a pK(a) of 6.7, suggesting that the glmS RNA reduces the pK(a) of the GlcN6P amine by 1.6 units in the ground state. We reevaluated previously obtained kinetic data and found the reaction pK(a) is 6.9, within error of the binding data. The data support a model where the reaction pK(a) corresponds to that of the GlcN6P amine. This observation has broader relevance for considering how the microenvironment of an RNA, despite its anionic character, can reduce the pK(a)s of functional groups for use in catalysis.
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