Characterization of amino acid‐derived betaines by electrospray ionization tandem mass spectrometry

Chary, V. Naresh; Kumar, Ch. Dinesh; Vairamani, M.; Prabhakar, S.

doi:10.1002/jms.2029

Cited by 25 publications

(14 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…So it is important to study the mass spectral characterization of dimethyl derivatives of all the amino acids. In the previous study, we have characterized all the amino acid derived betaines. The present study mainly focused on structural characterization of N , N ‐dimethyl amino acids by MS/MS and high‐resolution mass spectrometry (HRMS) analyses under ESI conditions.…”

Section: Introductionsupporting

confidence: 85%

Characterization of N,N‐dimethyl amino acids by electrospray ionization–tandem mass spectrometry

et al. 2015

Self Cite

View full text Add to dashboard Cite

Methylation is an essential metabolic process for a number of critical reactions in the body. Methyl groups are involved in the healthy function of the body life processes, by conducting methylation process involving specific enzymes. In these processes, various amino acids are methylated, and the occurrence of methylated amino acids in nature is diverse. Nowadays, mass-spectrometric-based identification of small molecules as biomarkers for diseases is a growing research. Although all dimethyl amino acids are metabolically important molecules, mass spectral data are available only for a few of them in the literature. In this study, we report synthesis and characterization of all dimethyl amino acids, by electrospray ionization-tandem mass spectrometry (MS/MS) experiments on protonated molecules. The MS/MS spectra of all the studied dimethyl amino acids showed preliminary loss of H2O + CO to form corresponding immonium ions. The other product ions in the spectra are highly characteristic of the methyl groups on the nitrogen and side chain of the amino acids. The amino acids, which are isomeric and isobaric with the studied dimethyl amino acids, gave distinctive MS/MS spectra. The study also included MS/MS analysis of immonium ions of dimethyl amino acids that provide information on side chain structure, and it is further tested to determine the N-terminal amino acid of the peptides.

show abstract

Section: Introductionsupporting

confidence: 85%

Characterization of N,N‐dimethyl amino acids by electrospray ionization–tandem mass spectrometry

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…The mixture was stirred on a magnetic stirrer at room temperature and 75 µL of iodomethane (171 mg, 1.2 mmole) added (Aurelio et al 2004; Naresh Chary et al 2012). The vial was loosely capped and the mixture stirred overnight at room temperature in the dark.…”

Section: Methodsmentioning

confidence: 99%

Structure elucidation of metabolite x17299 by interpretation of mass spectrometric data

et al. 2017

View full text Add to dashboard Cite

IntroductionA 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.ObjectivesThe aim of this work is to elucidate the chemical structure of x17299, a new compound by de novo interpretation of mass spectrometric data.MethodsAn 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.ResultsThe 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.ConclusionThe chemical structure of metabolite x17299 was determined to be l,l-TMAP.Electronic supplementary materialThe online version of this article (doi:10.1007/s11306-017-1231-x) contains supplementary material, which is available to authorized users.

show abstract

“… 33 The fragmentation of TMO, TML, and betaine ( Figure S-5B–E ), is consistent with reported fragmentation of betaine analogs. 34 …”

Section: Resultsmentioning

confidence: 99%

¹H NMR Metabolic Profiling of Earthworm (Eisenia fetida) Coelomic Fluid, Coelomocytes, and Tissue: Identification of a New Metabolite—Malylglutamate

et al. 2017

View full text Add to dashboard Cite

Earthworm metabolism is recognized as a useful tool for monitoring environmental insults and measuring ecotoxicity, yet extensive earthworm metabolic profiling using 1H nuclear magnetic resonance (NMR) spectroscopy has been limited in scope. This study aims to expand the embedded metabolic material in earthworm coelomic fluid, coelomocytes, and tissue to aid systems toxicology research. Fifty-nine metabolites within Eisenia fetida were identified, with 47 detected in coelomic fluid, 41 in coelomocytes, and 54 in whole-worm samples and tissue extracts. The newly detected but known metabolites 2-aminobutyrate, nicotinurate, Nδ,Nδ,Nδ-trimethylornithine, and trigonelline are reported along with a novel compound, malylglutamate, elucidated using 2D NMR and high-resolution MS/MS. We postulate that malylglutamate acts as a glutamate/malate store, chelator, and anionic osmolyte and helps to provide electrolyte balance.

show abstract

Characterization of amino acid‐derived betaines by electrospray ionization tandem mass spectrometry

Cited by 25 publications

References 19 publications

Characterization of N,N‐dimethyl amino acids by electrospray ionization–tandem mass spectrometry

Characterization of N,N‐dimethyl amino acids by electrospray ionization–tandem mass spectrometry

Structure elucidation of metabolite x17299 by interpretation of mass spectrometric data

¹H NMR Metabolic Profiling of Earthworm (Eisenia fetida) Coelomic Fluid, Coelomocytes, and Tissue: Identification of a New Metabolite—Malylglutamate

Contact Info

Product

Resources

About

Characterization of amino acid‐derived betaines by electrospray ionization tandem mass spectrometry

Cited by 25 publications

References 19 publications

Characterization of N,N‐dimethyl amino acids by electrospray ionization–tandem mass spectrometry

Characterization of N,N‐dimethyl amino acids by electrospray ionization–tandem mass spectrometry

Structure elucidation of metabolite x17299 by interpretation of mass spectrometric data

1H NMR Metabolic Profiling of Earthworm (Eisenia fetida) Coelomic Fluid, Coelomocytes, and Tissue: Identification of a New Metabolite—Malylglutamate

Contact Info

Product

Resources

About

¹H NMR Metabolic Profiling of Earthworm (Eisenia fetida) Coelomic Fluid, Coelomocytes, and Tissue: Identification of a New Metabolite—Malylglutamate