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Systematic identification of N-acetylheparosan oligosaccharides by tandem mass spectrometric fragmentation.
Rapid Commun Mass Spectrom. 2006; 20(2):267-74.RC

Abstract

Recently, a useful procedure for the preparation of both even- and odd-numbered series of N-acetylheparosan (NAH) oligosaccharides was established. The present report describes findings when these NAH oligosaccharides were subjected to comparative mass spectrometry (MS)/MS fragmentation analysis by matrix-assisted laser desorption/ionization (MALDI)-LIFT-time-of-flight (TOF)/TOF-MS/MS, and electrospray ionization (ESI) collision-induced dissociation (CID) MS/MS. The resultant fragment ions were systematically assigned to elucidate fragmentation characteristics. In the MALDI-LIFT-MS/MS experiments, all the NAH oligosaccharides underwent unique glycosidic cleavages that included B-Y ion cleavages (nomenclature system of Domon and Costello, Glycoconjugate J. 1988; 5: 397) at the C-1 side, and C-Z ion cleavages at the C-4 side, with respect to glucuronic acid (GlcA). In addition, (0,2)A and/or (0,2)X cross-ring cleavages were observed for relatively small oligosaccharides. The former observation clearly reflects the occurrence of a GlcA-N-acetylglucosamine (GlcNAc) alternating structure of NAH, while the latter feature implies the occurrence of the -beta-1-4-glucuronide linkage. Extensive glycosidic cleavages were also observed in the ESI-CID-MS/MS fragmentation, though cleavage specificity was less evident than in the case of MALDI-LIFT-TOF/TOF-MS/MS. The information obtained in this study should be valuable for understanding both biosynthetic and degradation processes of NAH and its derivatives including heparin and heparan sulfate, as well as artificially modified NAH oligosaccharides.

Authors+Show Affiliations

Glycostructure Analysis Team, Research Center for Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST), Central-2, 1-1-1 Umezono, Tsukuba, Ibaraki 305-8568, Japan.No affiliation info availableNo affiliation info available

Pub Type(s)

Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16345123

Citation

Minamisawa, Toshikazu, et al. "Systematic Identification of N-acetylheparosan Oligosaccharides By Tandem Mass Spectrometric Fragmentation." Rapid Communications in Mass Spectrometry : RCM, vol. 20, no. 2, 2006, pp. 267-74.
Minamisawa T, Suzuki K, Hirabayashi J. Systematic identification of N-acetylheparosan oligosaccharides by tandem mass spectrometric fragmentation. Rapid Commun Mass Spectrom. 2006;20(2):267-74.
Minamisawa, T., Suzuki, K., & Hirabayashi, J. (2006). Systematic identification of N-acetylheparosan oligosaccharides by tandem mass spectrometric fragmentation. Rapid Communications in Mass Spectrometry : RCM, 20(2), 267-74.
Minamisawa T, Suzuki K, Hirabayashi J. Systematic Identification of N-acetylheparosan Oligosaccharides By Tandem Mass Spectrometric Fragmentation. Rapid Commun Mass Spectrom. 2006;20(2):267-74. PubMed PMID: 16345123.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Systematic identification of N-acetylheparosan oligosaccharides by tandem mass spectrometric fragmentation. AU - Minamisawa,Toshikazu, AU - Suzuki,Kiyoshi, AU - Hirabayashi,Jun, PY - 2005/12/14/pubmed PY - 2006/2/24/medline PY - 2005/12/14/entrez SP - 267 EP - 74 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 20 IS - 2 N2 - Recently, a useful procedure for the preparation of both even- and odd-numbered series of N-acetylheparosan (NAH) oligosaccharides was established. The present report describes findings when these NAH oligosaccharides were subjected to comparative mass spectrometry (MS)/MS fragmentation analysis by matrix-assisted laser desorption/ionization (MALDI)-LIFT-time-of-flight (TOF)/TOF-MS/MS, and electrospray ionization (ESI) collision-induced dissociation (CID) MS/MS. The resultant fragment ions were systematically assigned to elucidate fragmentation characteristics. In the MALDI-LIFT-MS/MS experiments, all the NAH oligosaccharides underwent unique glycosidic cleavages that included B-Y ion cleavages (nomenclature system of Domon and Costello, Glycoconjugate J. 1988; 5: 397) at the C-1 side, and C-Z ion cleavages at the C-4 side, with respect to glucuronic acid (GlcA). In addition, (0,2)A and/or (0,2)X cross-ring cleavages were observed for relatively small oligosaccharides. The former observation clearly reflects the occurrence of a GlcA-N-acetylglucosamine (GlcNAc) alternating structure of NAH, while the latter feature implies the occurrence of the -beta-1-4-glucuronide linkage. Extensive glycosidic cleavages were also observed in the ESI-CID-MS/MS fragmentation, though cleavage specificity was less evident than in the case of MALDI-LIFT-TOF/TOF-MS/MS. The information obtained in this study should be valuable for understanding both biosynthetic and degradation processes of NAH and its derivatives including heparin and heparan sulfate, as well as artificially modified NAH oligosaccharides. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/16345123/Systematic_identification_of_N_acetylheparosan_oligosaccharides_by_tandem_mass_spectrometric_fragmentation_ L2 - https://doi.org/10.1002/rcm.2310 DB - PRIME DP - Unbound Medicine ER -