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Talanta. 2009 Apr 30;78(2):358-63. doi: 10.1016/j.talanta.2008.11.026. Epub 2008 Nov 27.

Combination of beta-elimination and liquid chromatography/quadrupole time-of-flight mass spectrometry for the determination of O-glycosylation sites.

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1
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong SAR, PR China.

Abstract

Determination of O-glycosylation sites in glycopeptides was developed by using two model compounds designed from mucin2 tandem repeat motif and erythropoietin. beta-Elimination/addition reaction using dimethylamine on glycosylated site through a Michael-type condensation produced efficient deglycosylation with appropriate chemical modification. The use of dimethylamine was efficient to release the O-linked glycan in a reaction time period of 2-6h at 55 degrees C. Peptide sequencing was then performed using the liquid chromatography/quadrupole time-of-flight mass spectrometry and MS-MS experiments. Interpretation of fragmentation pathways of the beta-elimination/addition products enabled straightforward recognition of glycosylation site. Compared to the fragmentation of corresponding native peptides, mass shift of -18 Da or +27 Da was clearly observed for the two kinds of beta-elimination/addition products of the glycosylated threonine. Dimethylamine was found to provide higher efficiency of beta-elimination/addition than methylamine and ammonia.

PMID:
19203595
DOI:
10.1016/j.talanta.2008.11.026
[Indexed for MEDLINE]
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