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Mass Spectrometry of Amines01:19

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In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule: a molecule with an odd number of nitrogen atoms produces a parent ion with an odd molecular weight. The remaining fragments have an even mass.
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In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...
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Stereoselective Amine-omics Using Heavy Atom Isotope Labeled l- and d-Marfey's Reagents.

Nitish R Mishra1, William G Gutheil1

  • 1Division of Pharmacology and Pharmaceutical Sciences, School of Pharmacy, University of Missouri─Kansas City, Kansas City, Missouri 64108, United States.

Journal of the American Society for Mass Spectrometry
|April 29, 2024
PubMed
Summary

A new method uses heavy-labeled Marfey's reagent for precise stereoisomer analysis of biological amines and amino acids. This technique enhances "amino-omics" studies by improving the identification and quantification of chiral compounds.

Keywords:
Marfey’s reagentheavy atom isotopeliquid chromatography−mass spectrometrymetabolomicsmethicillin-resistant Staphylococcus aureusstereochemistry

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Area of Science:

  • Biochemistry
  • Analytical Chemistry
  • Metabolomics

Background:

  • Biological amines and amino acids are crucial for numerous biochemical processes.
  • Analyzing stereoisomers of chiral amines and amino acids is vital for "amino-omics" but challenging due to limitations of achiral separation methods.
  • Previous work established Marfey's reagent for resolving amine and amino acid stereoisomers via LC-MS/MS.

Purpose of the Study:

  • To develop a heavy atom isotope-labeled Marfey's reagent approach for stereoselective detection and quantification of amines and amino acids.
  • To enhance the analytical capabilities for "amino-omics" by enabling precise stereoisomer identification.

Main Methods:

  • Synthesis of heavy (13C2) l-Marfey's (Hl-Mar) and heavy (2H3) d-Marfey's (Hd-Mar) reagents.
  • Derivatization of amine mixtures using both light and heavy Marfey's reagents.
  • Analysis by Liquid Chromatography-Quadrupole Time-of-Flight-High-Resolution Mass Spectrometry (LC-QToF-HRMS).
  • Comparative analysis of mass differences (light vs. heavy Marfey's adducts) and retention times to identify stereoisomers.

Main Results:

  • Successful synthesis of heavy-labeled Marfey's reagents (Hl-Mar and Hd-Mar).
  • Demonstrated ability to identify mono-, di-, and tri-Marfey's adducts based on mass differences.
  • Accurate stereoisomer identification through retention time differences between l- and d-Mar derivatives.
  • Application of the method to identify chiral and achiral components in a methicillin-resistant Staphylococcus aureus (MRSA) extract.

Conclusions:

  • The heavy atom isotope-labeled Marfey's reagent approach provides high analytical selectivity and reproducibility for amine and amino acid stereoisomer analysis.
  • This method significantly advances the capabilities for "amino-omics" research by enabling precise stereoisomer quantification.
  • The developed technique is robust and applicable to complex biological samples.