title: Recovery of free oligosaccharides from derivatives labeled by reductive amination.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kinki University, Higashi-osaka, Osaka 577-8502, Japan. suzuki@phar.kindai.ac.jp
authors.forename: Shigeo
authors.initials: S
authors.lastname: Suzuki
authors.forename: Takahiro
authors.initials: T
authors.lastname: Fujimori
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yodoshi
mesh_terms: D000081:Acetamides / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000032:analysis / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry; D002240:Carbohydrate Sequence; D006023:Glycoproteins / Q000032:analysis / Q000737:chemistry; D006801:Humans; D006861:Hydrogen Peroxide / Q000737:chemistry; D008320:Maltose / Q000032:analysis / Q000737:chemistry; D013058:Mass Spectrometry; D009844:Oligosaccharides / Q000032:analysis / Q000737:chemistry*; D011134:Polysaccharides / Q000032:analysis / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013696:Temperature; D013997:Time Factors
chemical_list: C092544:4-trifluoroacetamidoaniline; D000081:Acetamides; D000588:Amines; D000814:Aniline Compounds; D006023:Glycoproteins; D009844:Oligosaccharides; D011134:Polysaccharides; D008320:Maltose; D006861:Hydrogen Peroxide