Mass spectrometric glycan rearrangements
- PMID: 21560141
- DOI: 10.1002/mas.20337
Mass spectrometric glycan rearrangements
Abstract
Mass spectrometric rearrangement reactions have been reported for a large variety of compounds such as peptides, lipids, and carbohydrates. In the case of carbohydrates this phenomenon has been described as internal residue loss. Resulting fragment ions may be misinterpreted as fragments arising from conventional glycosidic bond cleavages, which may result in incorrect structural assignment. Therefore, awareness of the occurrence of glycan rearrangements is important for avoiding misinterpretation of tandem mass spectra. In this review mass spectrometric rearrangements of both derivatized and underivatized (native) oligosaccharide structures are discussed. Similar phenomena have been reported for glycopeptides, labeled glycan structures and other biomolecules containing a carbohydrate part. Rearrangements in oligosaccharides and glycoconjugates have been observed with different types of mass spectrometers. Most of the observed carbohydrate rearrangement reactions appear to be linked to the presence of a proton. Hence, tandem mass spectrometric analysis of alkali adducts or deprotonated ions often prevents rearrangement reactions, while they may happen with high efficacy with protonated glycoconjugates.
Copyright © 2011 Wiley Periodicals, Inc.
Similar articles
-
Hexose rearrangements upon fragmentation of N-glycopeptides and reductively aminated N-glycans.Anal Chem. 2009 Jun 1;81(11):4422-32. doi: 10.1021/ac900278q. Anal Chem. 2009. PMID: 19419147
-
Sodium-cationized oligosaccharides do not appear to undergo 'internal residue loss' rearrangement processes on tandem mass spectrometry.Rapid Commun Mass Spectrom. 1998;12(20):1520-32. doi: 10.1002/(SICI)1097-0231(19981030)12:20<1520::AID-RCM336>3.0.CO;2-W. Rapid Commun Mass Spectrom. 1998. PMID: 9796537
-
High-energy collision-induced fragmentation of complex oligosaccharides ionized by matrix-assisted laser desorption/ionization mass spectrometry.J Mass Spectrom. 1997 Feb;32(2):167-87. doi: 10.1002/(SICI)1096-9888(199702)32:2<167::AID-JMS472>3.0.CO;2-Q. J Mass Spectrom. 1997. PMID: 9102200
-
Glycoproteomics based on tandem mass spectrometry of glycopeptides.J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Apr 15;849(1-2):115-28. doi: 10.1016/j.jchromb.2006.09.041. Epub 2006 Oct 17. J Chromatogr B Analyt Technol Biomed Life Sci. 2007. PMID: 17049937 Review.
-
Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2007-2008.Mass Spectrom Rev. 2012 Mar-Apr;31(2):183-311. doi: 10.1002/mas.20333. Epub 2011 Aug 17. Mass Spectrom Rev. 2012. PMID: 21850673 Review.
Cited by
-
PARP7 and Mono-ADP-Ribosylation Negatively Regulate Estrogen Receptor α Signaling in Human Breast Cancer Cells.Cells. 2021 Mar 11;10(3):623. doi: 10.3390/cells10030623. Cells. 2021. PMID: 33799807 Free PMC article.
-
Gas-Phase Fragmentation of Cyclic Oligosaccharides in Tandem Mass Spectrometry.Molecules. 2019 Jun 14;24(12):2226. doi: 10.3390/molecules24122226. Molecules. 2019. PMID: 31207901 Free PMC article. Review.
-
Characterization of Isomeric Glycans by Reversed Phase Liquid Chromatography-Electronic Excitation Dissociation Tandem Mass Spectrometry.J Am Soc Mass Spectrom. 2018 Jun;29(6):1295-1307. doi: 10.1007/s13361-018-1943-9. Epub 2018 Apr 13. J Am Soc Mass Spectrom. 2018. PMID: 29654534 Free PMC article.
-
Site specific N-glycan profiling of NeuAc(α2-6)-Gal/GalNAc-binding bark Sambucus nigra agglutinin using LC-MSn revealed differential glycosylation.Glycoconj J. 2016 Dec;33(6):907-915. doi: 10.1007/s10719-016-9698-7. Epub 2016 Jul 6. Glycoconj J. 2016. PMID: 27384337
-
"Cross-glycosylation" of proteins in Bacteroidales species.Glycobiology. 2013 May;23(5):568-77. doi: 10.1093/glycob/cws172. Epub 2012 Dec 19. Glycobiology. 2013. PMID: 23258847 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
