Structure elucidation of metabolite x17299 by interpretation of mass spectrometric data
| Autor: | Douglas R. Toal, Anne M. Evans, Qibo Zhang, Lisa A. Ford |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Metabolite structure elucidation Stereochemistry Endocrinology Diabetes and Metabolism Metabolite Chemical structure Clinical Biochemistry Orbitrap Mass spectrometry 01 natural sciences Biochemistry law.invention 03 medical and health sciences chemistry.chemical_compound Metabolomics x17299 law Derivatization Mass spectrum interpretation Chromatography Molecular mass 010401 analytical chemistry N N N-Trimethyl-l-alanyl-l-proline betaine 0104 chemical sciences 030104 developmental biology chemistry Mass spectrum Original Article |
| Zdroj: | Metabolomics |
| ISSN: | 1573-3890 1573-3882 |
| DOI: | 10.1007/s11306-017-1231-x |
| Popis: | Introduction A major bottleneck in metabolomic studies is metabolite identification from accurate mass spectrometric data. Metabolite x17299 was identified in plasma as an unknown in a metabolomic study using a compound-centric approach where the associated ion features of the compound were used to determine the true molecular mass. Objectives The aim of this work is to elucidate the chemical structure of x17299, a new compound by de novo interpretation of mass spectrometric data. Methods An Orbitrap Elite mass spectrometer was used for acquisition of mass spectra up to MS4 at high resolution. Synthetic standards of N,N,N-trimethyl-l-alanyl-l-proline betaine (l,l-TMAP), a diastereomer, and an enantiomer were chemically prepared. Results The planar structure of x17299 was successfully proposed by de novo mechanistic interpretation of mass spectrometric data without any laborious purification and nuclear magnetic resonance spectroscopic analysis. The proposed structure was verified by deuterium exchanged mass spectrometric analysis and confirmed by comparison to a synthetic standard. Relative configuration of x17299 was determined by direct chromatographic comparison to a pair of synthetic diastereomers. Absolute configuration was assigned after derivatization of x17299 with a chiral auxiliary group followed by its chromatographic comparison to a pair of synthetic standards. Conclusion The chemical structure of metabolite x17299 was determined to be l,l-TMAP. Electronic supplementary material The online version of this article (doi:10.1007/s11306-017-1231-x) contains supplementary material, which is available to authorized users. |
| Databáze: | OpenAIRE |
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