通过循环色谱法分离人乳寡糖。首次从该来源中分离出乳糖-N-新二岩藻六糖II和3'-半乳糖基乳糖。

Separation of human milk oligosaccharides by recycling chromatography. First isolation of lacto-N-neo-difucohexaose II and 3'-Galactosyllactose from this source.

作者信息

Donald A S, Feeney J

机构信息

Division of Immunochemical Genetics, MRC Clinical Research Centre, Watford Road, Harrow, Middlesex HA1 3UJ (United Kingdom).

出版信息

Carbohydr Res. 1988 Jul 15;178:79-91. doi: 10.1016/0008-6215(88)80103-4.

DOI:10.1016/0008-6215(88)80103-4

PMID:3274083

Abstract

Lacto-N-neo-difucohexaose II, beta-D-Galp-(1----4)-[alpha-L-Fucp-(1----3)]-beta-D-Glcp-NAc-(1----3)-beta-D-Galp-(1----4)-[alpha-L-Fucp-(1----3)]-D-Glc, and 3'-galactosyllactose, beta-D-Galp-(1----3)-beta-D-Galp-(1----4)-D-Glc, were isolated for the first time from human milk by means of a recycling chromatography technique. Through this method, carried out mainly on columns of K+ ion-exchange resins and either Bio-Gel P-4 or TSK 40 W(S) gel filtration media, up to one gram of an oligosaccharide mixture could be handled and lacto-N-neo-difucohexaose II separated from isomeric lacto-N-difucohexaose I, alpha-L-Fucp-(1----2)-beta-D-Galp-(1----3)-[alpha-L-Fucp-(1----4)]-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-D-Glc, and II, beta-D-Galp-(1----3)-[alpha L-Fucp-(1----4)]-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-[alpha-L-Fucp-(1----3)]-D-Glc. This method also permitted resolution of isomeric mixtures of the trisaccharides 2'-fucosyllactose, alpha-L-Fucp-(1----2)-beta-D-Galp-(1----4)-D-Glc, and 3-fucosyllactose, beta-D-Galp-(1----4)-[alpha-L-Fucp-(1----3)]-D-Glc, the tetrasaccharides lacto-N-tetraose, beta-D-Galp-(1----3)-beta-D-GlcpNac-(1----3)-beta-D-Galp-(1----4)-D-Glc, and lacto-N-neo-tetraose, beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-D-Glc, and the pentaoses lacto-N-fucopentaose I, alpha-L-Fucp-(1----2)-beta-D-Galp-(1----3)-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-D-Glc, II, beta-D-Galp-(1----3)-[alpha-L-Fucp-(1----4)]-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-D-Glc, and III, beta-D-Galp-(1----4)-[alpha-L-Fucp-(1----3)]-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-D-Glc, which have proved difficult if not impossible to separate by other means. The isolation of these and other milk oligosaccharides is described herein. The 500-MHz 1H-n.m.r. spectra of lacto-N-neo-difucohexaose II and 3'-galactosyllactose, and their alditols, are recorded. 1H-n.m.r. data on some other milk oligosaccharides, both natural and reduced, are also given.

摘要

通过循环色谱技术首次从人乳中分离出乳糖 - N - 新二岩藻六糖II（β - D - 半乳糖 - (1→4)-[α - L - 岩藻糖基 - (1→3)] - β - D - 葡萄糖胺 - (1→3)-β - D - 半乳糖 - (1→4)-[α - L - 岩藻糖基 - (1→3)] - D - 葡萄糖）、3'- 半乳糖基乳糖（β - D - 半乳糖 - (1→3)-β - D - 半乳糖 - (1→4)-D - 葡萄糖）。通过该方法，主要在钾离子交换树脂柱以及Bio - Gel P - 4或TSK 40 W(S)凝胶过滤介质上进行，一次可处理多达一克的寡糖混合物，并将乳糖 - N - 新二岩藻六糖II与异构的乳糖 - N - 二岩藻六糖I（α - L - 岩藻糖基 - (1→2)-β - D - 半乳糖 - (1→3)-[α - L - 岩藻糖基 - (1→4)] - β - D - 葡萄糖胺 - (1→3)-β - D - 半乳糖 - (1→4)-D - 葡萄糖）和II（β - D - 半乳糖 - (1→3)-[α - L - 岩藻糖基 - (1→4)] - β - D - 葡萄糖胺 - (1→3)-β - D - 半乳糖 - (1→4)-[α - L - 岩藻糖基 - (1→3)] - D - 葡萄糖）分离。该方法还可分离三糖2'- 岩藻糖基乳糖（α - L - 岩藻糖基 - (1→2)-β - D - 半乳糖 - (1→4)-D - 葡萄糖）和3 - 岩藻糖基乳糖（β - D - 半乳糖 - (1→4)-[α - L - 岩藻糖基 - (1→3)] - D - 葡萄糖）、四糖乳糖 - N - 四糖（β - D - 半乳糖 - (1→3)-β - D - 葡萄糖胺 - (1→3)-β - D - 半乳糖 - (1→4)-D - 葡萄糖）和乳糖 - N - 新四糖（β - D - 半乳糖 - (1→4)-β - D - 葡萄糖胺 - (1→3)-β - D - 半乳糖 - (1→4)-D - 葡萄糖）以及戊糖乳糖 - N - 岩藻戊糖I（α - L - 岩藻糖基 - (1→2)-β - D - 半乳糖 - (1→3)-β - D - 葡萄糖胺 - (1→3)-β - D - 半乳糖 - (1→4)-D - 葡萄糖）、II（β - D - 半乳糖 - (1→3)-[α - L - 岩藻糖基 - (1→4)] - β - D - 葡萄糖胺 - (1→3)-β - D - 半乳糖 - (