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Sensitive Analysis of Oligosaccharides Derivatized with 4‐Aminobenzoic Acid 2‐(Diethylamino)ethyl Ester by Matrix‐assisted Laser Desorption/Ionization Mass Spectrometry
Author(s) -
Takao Toshifumi,
Tambara Yanet,
Nakamura Akihiro,
Yoshino Kenichi,
Fukuda Hiroyuki,
Fukuda Masafumi,
Shimonishi Yasutsugu
Publication year - 1996
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(199604)10:6<637::aid-rcm544>3.0.co;2-9
Subject(s) - chemistry , derivatization , oligosaccharide , mass spectrometry , chromatography , electrospray ionization , matrix assisted laser desorption/ionization , reductive amination , desorption , organic chemistry , catalysis , adsorption
A sensitive detection method for oligosaccharides using matrix‐assisted laser desorption/ionization mass spectrometry has been developed. The method involves the derivatization of oligosaccharides with 4‐aminobenzoic acid 2‐(diethylamino)ethyl ester (ABDEAE) by reductive amination, a technique which was initially developed for high‐sensitivity detection of oligosaccharides by electrospray ionization mass spectrometry (K. Yoshino, T. Takao, H. Murata and Y. Shimonishi, Anal. Chem. 67, 4028 (1995)). Experiments using a high‐mannose‐type N ‐linked oligosaccharide (Man 8 GlcNAc 2 ) as a model oligosaccharide showed that derivatization with ABDEAE gave 400‐, 80‐, and 20‐fold increases in molecular ion abundance over the underivatized oligosaccharide and the oligosaccharide derivatized with 2‐aminopyridine and 4‐aminobenzoic acid ethyl ester respectively. ABDEAE‐derivatized maltoheptaose could be detected at a level of 10 fmol, which represents a 1000‐fold increase in sensitivity over the underivatized oligosaccharide. Moreover, ABDEAE derivatization also allows in‐source fragmentation to give the specific ions produced by glycosidic cleavage.