The unexpected racemization and hydrogen–deuterium exchange of the hydrogen at the α-carbon of proline analogs containing the 5-azoniaspiro[4.4]nonyl-group
| Autor: | Bartosz Setner, Zbigniew Szewczuk, Lucjan B. Jerzykiewicz, Marek Lisowski, Magdalena Wierzbicka |
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| Rok vydání: | 2018 |
| Předmět: |
Aqueous solution
010401 analytical chemistry Organic Chemistry 010402 general chemistry Mass spectrometry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Deuterium Hydrogen–deuterium exchange Isotopologue Ammonium Physical and Theoretical Chemistry Triethylamine Racemization |
| Zdroj: | Organic & Biomolecular Chemistry. 16:825-831 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | Recently, we developed a novel non-fragmenting quaternary ammonium ionization tag for the mass spectrometric sensitive sequencing of peptides, based on the N-spiro proline residue (5-azoniaspiro[4.4.]nonyl-carbonyl). Herein, we present an unexpected racemization and the hydrogen-deuterium exchange (HDX) at the α-C atom of the proline derivative under basic aqueous conditions (1% water solution of triethylamine). The deuterium atom, substituted for the α-C atom, does not undergo back-exchange under acidic aqueous conditions which makes the deuterated isotopologue a promising stabile isotope-coded internal standard for quantitative analysis by mass spectrometry. The applicability of the prepared isotopologues of the quaternary ammonium salt labeled peptides for quantification experiments using the isotopic dilution method was also examined. |
| Databáze: | OpenAIRE |
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