Derivatization Procedures for Reducing Oligosaccharides, Part 4: Use of Glycosylamines in a Reversible Derivatization of Oligosaccharides with the 9-Fluorenylmethoxycarbonyl Group, and Hplc Separations of the Derivatives
作者:
Elisabeth Kallin,
Hans Lönn,
Thomas Norberg,
Torbjörn Sund,
Mons Lundqvist,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1991)
卷期:
Volume 10,
issue 3
页码: 377-386
ISSN:0732-8303
年代: 1991
DOI:10.1080/07328309108543915
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
A new, reversible derivatization procedure for reducing oligosaccharides was developed. Reaction of the model compound lacto-N-tetraose (β-D-Gal-(1→3)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-D-Glc) with aqueous ammonium bicarbonate gave the corresponding β-glycosylamine, which was reacted with fluorenylmethoxycarbonyl chloride to give anN-fluorenyl-methoxycarbonyl β-glycosylamine (FMOC derivative). The free oligosaccharide could be recovered in high yield from the FMOC derivative by brief treatment with 15% aqueous ammonia. Complex oligosaccharide mixtures from human milk were derivatized with the new procedure, and excellent separations of the derivatives on straight-phase silica HPLC columns were achieved.
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