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Structural assignment of isomeric 2-aminopyridine derivatized monosialylated biantennary N-linked oligosaccharides using negative-ion MSn spectral matching

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Title: Structural assignment of isomeric 2-aminopyridine derivatized monosialylated biantennary N-linked oligosaccharides using negative-ion MSn spectral matching
Authors: Deguchi, Kisaburo1 Browse this author
Takegawa, Yasuhiro Browse this author →KAKEN DB
Ito, Hiroki Browse this author
Miura, Nobuaki Browse this author →KAKEN DB
Yoshioka, Shinji Browse this author →KAKEN DB
Nagai, Shinji Browse this author
Nakagawa, Hiroaki Browse this author
Nishimura, Shin-Ichiro Browse this author →KAKEN DB
Authors(alt): 出口, 喜三郎1
Issue Date: 2006
Publisher: John Wiley & Sons
Journal Title: Rapid Communications in Mass Spectrometry
Volume: 20
Issue: 3
Start Page: 412
End Page: 418
Publisher DOI: 10.1002/rcm.2320
PMID: 16381065
Abstract: To investigate the possibility of structural assignment based on negative-ion MSn spectral matching, four isomers of 2-aminopyridine-derivatized (PA) monosialylated oligosaccharides (i.e., complex type N-glycans with an α2-3 or α2-6 linked sialic acid on α1-6 or α1-3 antennae) were analyzed by using high-performance liquid chromatography/electrospray ion trap time-of-flight mass spectrometry(HPLC/ESI-IT-TOF MS). The negative ion [M-2H]2- is observed dominantly in the MS1 spectra without the loss of a sialic acid. The MS2 spectra derived from it are sufficiently reproducible that MS2 spectral matching based on correlation coefficients can be applied to the assignment of these isomers. The isomers containing a sialic acid on α1-6 or α1-3 antennae can be distinguished by MS2 spectral matching, but the α2-3 and α2-6 linkage types of sialic acid cannot be distinguished by their MS2 spectra. However, MS3 spectra derived from fragment ions containing a sialic acid (i.e., C4- and D-type ions) clearly differentiate the α2-3 and α2-6 linkage types of sialic acid in their MS3 spectral patterns. This difference might be rationalized in terms of a proton transfer from the reducing-end mannose to the negatively-charged sialic acid. These two moieties are very close in the structural conformations of the precursor C4-type fragment ions, as predicted by molecular mechanics calculations. Thus, negative-ion MSn (n=2, 3) spectral matching was proven to be useful for the structural assignment of these four monosialylated PA N-glycan isomers.
Rights: Copyright © 2006 John Wiley & Sons, Inc., Rapid Communications in Mass Spectrometry, vol.20(3),p412-418
Relation: http://www.interscience.wiley.com/
Type: article (author version)
URI: http://hdl.handle.net/2115/5844
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 出口 喜三郎

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