Document Detail

Derivatization for stabilizing sialic acids in MALDI-MS.
MedLine Citation:
PMID:  16053310     Owner:  NLM     Status:  MEDLINE    
While matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) is useful in oligosaccharide analysis, the sialic acid, or N-acetylneuraminic acid (NANA), moiety of an oligosaccharide is liable to dissociation in- or postsource during mass measurement. In this study, we tried to stabilize the moiety by amidation, as in the case of peptides (Sekiya, S.; Wada, Y. Tanaka, K. Anal. Chem. 2004, 76, 5894-5902), and found 4-(4,6-dimethoxy-1,3,5-triazin-2yl)-4-methylmorpholinium chloride to be a desirable condensing agent. Amidation stabilized the glycosidic bond with NANA and suppressed its preferential cleavage by in-source decay, postsource decay, or collision-induced dissociation. In addition, the suppressed dissociation considerably improved the yield of the B/Y type ions for structural analysis by MS/MS. These results demonstrate that amidation is an effective derivatization to reinforce the structural analysis of sialylated oligosaccharides by MALDI-MS. In addition, amidation with (15)N-labeled ammonium chloride decreases the mass shift from the acid to amide form to just 0.013, reducing the complexity of mass spectral interpretation and database searching.
Sadanori Sekiya; Yoshinao Wada; Koichi Tanaka
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Analytical chemistry     Volume:  77     ISSN:  0003-2700     ISO Abbreviation:  Anal. Chem.     Publication Date:  2005 Aug 
Date Detail:
Created Date:  2005-08-01     Completed Date:  2007-03-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0370536     Medline TA:  Anal Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4962-8     Citation Subset:  IM    
Koichi Tanaka Mass Spectrometry Research Laboratory, Shimadzu Corporation, Nakagyo-ku, Kyoto 604-8511, Japan.
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MeSH Terms
Carbohydrate Sequence
Chromatography, High Pressure Liquid
Oligosaccharides / chemistry
Polysaccharides / chemistry
Sialic Acids / analysis*,  chemistry*
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / methods*
Transferrin / chemistry
Reg. No./Substance:
0/Oligosaccharides; 0/Polysaccharides; 0/Sialic Acids; 11096-37-0/Transferrin

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