通过氢-1和碳-13核磁共振光谱法确定的四种人乳八糖、九糖和十一糖的一级结构。

Primary structure of four human milk octa-, nona-, and undeca-saccharides established by 1H- and 13C-nuclear magnetic resonance spectroscopy.

作者信息

Strecker G, Fièvre S, Wieruszeski J M, Michalski J C, Montreuil J

机构信息

Laboratoire de Chimie Biologique (Unité Mixte de Recherche du C.N.R.S.No 111), Université des Sciences et Techniques de Lille Flandres-Artois, Villeneuve d'Ascq, France.

出版信息

Carbohydr Res. 1992 Mar 16;226(1):1-14. doi: 10.1016/0008-6215(92)84050-3.

DOI:10.1016/0008-6215(92)84050-3

PMID:1499015

Abstract

The structures of two octasaccharides, one nonasaccharide, and one undecasaccharide, isolated from human milk, have been investigated by 1H- and 13C-nuclear magnetic resonance spectroscopy. The structures of these oligosaccharides are: beta-D-Galp-(1----4)-[alpha-L-Fucp- (1----3)]-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-[alpha-L-Fucp+ ++- (1----3)]-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-D-Glc; 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)]-beta-D-GlcpNAc-(1----3)-beta -D-Galp- (1----4)-D-Glc; beta-D-Galp-(1----4)-[alpha-L-Fucp-(1----3)]-beta-D-GlcpNAc-(1---- 6)-(alpha - L-Fucp-(1----2)-beta-D-Gal-(1----3)-[alpha-L-Fucp-(1----4)]- beta-D-GlcpNAc- (1----3))-beta-D-Galp-(1----4)-D-Glc; and alpha-L-Fucp-(1----2)-beta-D-Galp-(1----3)-beta-D-GlcpNAc-(1----3) -beta-D- Galp-(1----4)-[alpha-L-Fucp-(1----3)]-beta-D-GlcpNAc-(1----6)-[alp ha-L- Fucp-(1----2)-beta-D-Galp-(1----3)-beta-D-GlcpNAc-(1----3)]-beta-D -Galp- (1----4)-D-Glc. The two octasaccharides have been previously isolated from human milk as a mixture, and in a pure form from new-born feces, but the n.m.r. data were not provided. These two octasaccharides display the di-Lewis X and the composite Lewis A-Lewis X antigenic determinant, previously described as neo-antigens of adenocarcinoma cell lines.

摘要

从人乳中分离出的两种八糖、一种九糖和一种十一糖的结构，已通过1H-和13C-核磁共振光谱进行了研究。这些寡糖的结构如下：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)]-β-D-葡萄糖胺-(1→3)-β-D-半乳糖-(1→4)-D-葡萄糖；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)]-β-D-葡萄糖胺-(1→3)-β-D-半乳糖-(1→4)-D-葡萄糖；β-D-半乳糖-(1→4)-[α-L-岩藻糖基-(1→3)]-β-D-葡萄糖胺-(1→6)-(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；以及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)-[α-L-岩藻糖基-(1→3)]-β-D-葡萄糖胺-(1→6)-[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。这两种八糖此前已从人乳中作为混合物分离出来，并从新生儿粪便中以纯形式分离出来，但未提供核磁共振数据。这两种八糖显示出二-Lewis X以及复合Lewis A-Lewis X抗原决定簇，此前被描述为腺癌细胞系的新抗原。