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Selective detection of carbohydrates and their peptide conjugates by ESI-MS using synthetic quaternary ammonium salt derivatives of phenylboronic acids.
Autorzy
Rok wydania
2014
Czasopismo
Journal of the American Society for Mass Spectrometry
Numer woluminu
25
Strony
966-976
DOI
10.1007/s13361-014-0857-4
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
We present new tags based on the derivatives of phenylboronic acid and apply them for the selective detection of sugars and peptide-sugar conjugates in mass spectrometry. We investigated the binding of phenylboronic acid and its quaternary ammonium salt (QAS) derivatives to carbohydrates and peptidederived Amadori products by HR-MS and MS/MS experiments. The formation of complexes between sugar or sugar-peptide conjugates and synthetic tags was confirmed on the basis of the unique isotopic distribution resulting from the presence of boron atom. Moreover, incorporation of a quaternary ammonium salt dramatically improved the efficiency of ionization in mass spectrometry. It was found that the formation of a complex with phenylboronic acid stabilizes the sugar moiety in glycated peptides, resulting in simplification of the fragmentation pattern of peptide-derived Amadori products. The obtained results suggest that derivatization of phenylboronic acid as QAS is a promising method for sensitive ESI-MS detection of carbohydrates and their conjugates formed by nonenzymatic glycation or glycosylation.
Słowa kluczowe
Quaternary ammonium salts, Mass spectrometry, Solid phase synthesis, Amadori products, Nonenzymatic glycation, Sugars, Phenylboronic acids
Licencja otwartego dostępu
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Pełny tekst licencji: https://creativecommons.org/licenses/by/3.0/pl/legalcode
Adres publiczny
http://dx.doi.org/10.1007/s13361-014-0857-4
Strona internetowa wydawcy
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