1599463-50-9Relevant academic research and scientific papers
Selective detection of carbohydrates and their peptide conjugates by esi-ms using synthetic quaternary ammonium salt derivatives of Phenylboronic acids
Kijewska, Monika,Kuc, Adam,Kluczyk, Alicja,Waliczek, Mateusz,Man-Kupisinska, Aleksandra,Lukasiewicz, Jolanta,Stefanowicz, Piotr,Szewczuk, Zbigniew
, p. 966 - 976 (2014)
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 peptide-derived 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 non-enzymatic glycation or glycosylation. [Figure not available: see fulltext.]
