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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.
Autorzy
Rok wydania
2018
Czasopismo
Organic and Biomolecular Chemistry
Numer woluminu
16
Strony
825-831
DOI
10.1039/C7OB02926H
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Recently, we developed a novel non-fragmenting quaternary ammonium ionization tag, for 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 at basic aqueous conditions (1% water solution of triethylamine). The deuterium atom, substituted for the α-C atom, does not undergo back exchange at acidic aqueous conditions what 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 salts labeled peptides for quantification experiments using isotopic dilution method was also examined.
Adres publiczny
http://dx.doi.org/10.1039/C7OB02926H
Strona internetowa wydawcy
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