Journal
CARBOHYDRATE RESEARCH
Volume 333, Issue 1, Pages 59-71Publisher
ELSEVIER SCI LTD
DOI: 10.1016/S0008-6215(01)00115-X
Keywords
glycosaminoglycan (GAG); oxime formation; reductive hydroxyamination; 3-methoxy-benzylhydroxylamine derivatives; 7-hydroxycoumarylhydroxylamine derivatives; HPLC; electrospray-ionization mass spectrometry (ESIMS)
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The reductive oxyamination of model glycan structures has been investigated as a mild, alternative tagging procedure to reductive amination using O-(4-nitrobenzyl)-hydroxylamine. Grime formation was quantitative, but the reduction step did not always go to completion. Novel O- and N-substituted 7-hydroxycoumaryl- and 3-methoxybenzylhydroxylamines were synthesized and shown to couple quantitatively with model saccharides by oxime formation and reductive hydroxyamination, respectively, under very mild, aqueous conditions. The fluorescent derivatives produced show good chromatographic and mass spectrometric properties. Both procedures are suitable for the labeling of carbohydrates and oligosaccharide fragments from glycosaminoglycan structures, such as heparin and heparan sulfate. (C) 2001 Elsevier Science Ltd. All rights reserved.
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