ArticleMagnetic resonance in chemistry : MRC2015
Chemoselective detection and discrimination of carbonyl-containing compounds in metabolite mixtures by 1H-detected 15N nuclear magnetic resonance.
Article in Magnetic resonance in chemistry : MRC, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- NMR-Based Stable Isotope Tracing of Cancer Metabolism.Methods in molecular biology (Clifton, N.J.) · 2025Article
- NMR-based isotope editing, chemoselection and isotopomer distribution analysis in stable isotope resolved metabolomics.Methods (San Diego, Calif.) · 2022Review
- Innovative Application of Metabolomics on Bioactive Ingredients of Foods.Foods (Basel, Switzerland) · 2022Review
- NMR Analysis of Carboxylate Isotopomers ofAnalytical chemistry · 2021Article
- Quantitative NMR-Based Biomedical Metabolomics: Current Status and Applications.Molecules (Basel, Switzerland) · 2020Review
- Isomeric Differentiation and Acidic Metabolite Identification by Piperidine-Based Tagging, LC-MS/MS, and Understanding of the Dissociation Chemistries.Analytical chemistry · 2020Article
- NMR and MS-based Stable Isotope-Resolved Metabolomics and Applications in Cancer Metabolism.Trends in analytical chemistry : TRAC · 2019Article
- Metabolic Labeling of Cultured Mammalian Cells for Stable Isotope-Resolved Metabolomics: Practical Aspects of Tissue Culture and Sample Extraction.Methods in molecular biology (Clifton, N.J.) · 2019Article
- Stable Isotope-Resolved Metabolomics by NMR.Methods in molecular biology (Clifton, N.J.) · 2019Article
- Quantitative profiling of carbonyl metabolites directly in crude biological extracts using chemoselective tagging and nanoESI-FTMS.The Analyst · 2017Article
- NMR-based Stable Isotope Resolved Metabolomics in systems biochemistry.Archives of biochemistry and biophysics · 2017Review
- Knowns and unknowns in metabolomics identified by multidimensional NMR and hybrid MS/NMR methods.Current opinion in biotechnology · 2017Review
- The future of NMR-based metabolomics.Current opinion in biotechnology · 2017Review
- Recent Advances in NMR-Based Metabolomics.Analytical chemistry · 2017Review
- Review
- Applications of NMR spectroscopy to systems biochemistry.Progress in nuclear magnetic resonance spectroscopy · 2016Review
- Two elephants in the room: new hybrid nuclear magnetic resonance and mass spectrometry approaches for metabolomics.Current opinion in clinical nutrition and metabolic care · 2015Review
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8 authors.
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Abstract
NMR spectra of mixtures of metabolites extracted from cells or tissues are extremely complex, reflecting the large number of compounds that are present over a wide range of concentrations. Although multidimensional NMR can greatly improve resolution as well as improve reliability of compound assignments, lower abundance metabolites often remain hidden. We have developed a carbonyl-selective aminooxy probe that specifically reacts with free keto and aldehyde functions, but not carboxylates. By incorporating (15)N in the aminooxy functional group, (15)N-edited NMR was used to select exclusively those metabolites that contain a free carbonyl function while all other metabolites are rejected. Here, we demonstrate that the chemical shifts of the aminooxy adducts of ketones and aldehydes are very different, which can be used to discriminate between aldoses and ketoses, for example. Utilizing the 2-bond or 3-bond (15)N-(1)H couplings, the (15)N-edited NMR analysis was optimized first with authentic standards and then applied to an extract of the lung adenocarcinoma cell line A549. More than 30 carbonyl-containing compounds at NMR-detectable levels, six of which we have assigned by reference to our database. As the aminooxy probe contains a permanently charged quaternary ammonium group, the adducts are also optimized for detection by mass spectrometry. Thus, this sample preparation technique provides a better link between the two structural determination tools, thereby paving the way to faster and more reliable identification of both known and unknown metabolites directly in crude biological extracts.
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