This study examined chemical regeneration of free oligosaccharides from their fluorescent derivatives prepared by reductive amination with various aromatic amines. Maltose derivatives of ethyl 4-aminobenzoate (p-ABEE), 2-aminobenzonitrile (o-ABN), 4-aminobenzonitrile (p-ABN), 7-amino-4-methylcoumarin (AMC), 2-aminobenzoic acid (o-ABA), 2-aminobenzamide (o-ABAD), 2-aminopyridine (AP), and 8-aminonaphthalene-1,3,6-trisulfonate (ANTS) were incubated at 30 degrees C with an aqueous solution of hydrogen peroxide/acetic acid. Recoveries of maltose from p-ABEE, p-ABN, and AMC derivatives were fairly good and gave approximately 90% of maltose. Recoveries of maltose from its o-substituted aniline (o-ABA, o-ABAD, and o-ABN) derivatives were 5-40%, but maltose was unrecoverable from AP and ANTS derivatives. Nevertheless, prior treatment of an AP derivative with cyanogen bromide enabled the regeneration of maltose in high yields. As an application, p-ABEE-labeled N-glycans from some glycoproteins separated on an amide column were identified by converting peak components to their AP derivatives via free saccharides and following mapping by reversed-phase chromatography.
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http://dx.doi.org/10.1016/j.ab.2006.04.013 | DOI Listing |
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