Journal
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
Volume 25, Issue 6, Pages 966-976Publisher
SPRINGER
DOI: 10.1007/s13361-014-0857-4
Keywords
Quaternary ammonium salt; Mass spectrometry; Solid phase synthesis; Amadori products; Non-enzymatic glycation; Sugars; Phenylboronic acids
Funding
- Faculty of Chemistry, University of Wroclaw from the Ministry of Science and Higher Education of Poland [2274/M/WCH/12]
- National Science Centre of Poland [UMO-2012/07/D/ST5/002324]
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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.
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