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Preparation of Oligosaccharaide Units Library Involved in Glycoconjugate and Its Utilization

复合糖低聚糖单元库的制备及其应用

基本信息

批准号：
08660134
负责人：
USUI Taichi
金额：
$ 1.47万
依托单位：
Shizuoka University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1996
资助国家：
日本
起止时间：
1996 至 1997
项目状态：
已结题

项目摘要

We established some synthetic routes of di-, tri, and tetrasaccharides, which are involved in glycoconjugate, through glycosidase-mediated transglycosylation and glycosyltransferase. These synthetic oligosaccharides were used for preparing glycopolymer as probes in carbohydrate-protein interaction studies.1. Mucin-type oligsaccharideGalbeta1-3 (GlcNAcbeta1-6) GalNAcalpha-OC_6H_4NO_2-p (1), whichis a carbohydrate region of mucin type 2 core, was enzymatically by the consecutive elongation of Gal and GlcNAcresidues to GalNAcalpha-OC_6H_4NO_2-p in two stages. Galbeta1-3GalNAcalpha-OC_6H_4NO_2-p (2) was firstly prepared by using galactosyl ation from lactose to GalNAcalpha-OC_6H_4NO_2-p. The resulting 2 was transformed into the desired compound 1 through Nocardia orientalis beta-N-acetylhexiosaminidase-mediated transglycosylation.2. N-Acetylglucosdaminyl trisaccharide3'-O-beta-N-acetylglucosaminyl-N-acetyllactosamine glycoside (3, GlcNAcbeta1-3Galbeta1-4GlcNAcbeta-OC_6H_4NO_2-p), which is the common trisaccharide unit of poly-N-acetyllactosamine, was synthesized through N-acetylglucosaminyl transfer by beta-N-acetylhexosaminidase from N.orientalis. In this case, when an inclusion complex of p-nitrophenyl beta-N-acetyllactosamine acceptor with alpha-cyclodextrin was used, the regioselectivity of glycosidase-mediated formation of the desired trisaccharide glycoside (3) was substantially changed.3. GlycopolymerN-Acetyllactosamine and its related compounds were used to transform into artificial glycopolymer. Two types of glycopolymers, whose main chain are polyacryl chain and polyglutamic scid peptide chain, were synthesized and used as modelin oligosaccharide-lection analysis. These water-soluble glycopolymers were shwon to interact specifically with the corresponding lectin, no matter how many side chains of the polymers are short-chain length such as disaccharide unit.

我们建立了通过糖苷酶介导的转糖基化和糖基转移酶合成糖缀合物中的二糖、三糖和四糖的路线。这些人工合成的寡糖被用来制备糖聚合物，作为研究糖-蛋白质相互作用的探针.粘蛋白型寡糖Galbeta 1 -3（GlcNAc beta1 -6）GalNAcalpha-OC_6 H_4 NO_2-p（1）是粘蛋白2型核心的一个糖区，由Gal和GlcNA的连续延伸酶解生成GalNAcalpha-OC_6 H_4 NO_2-p。首先将乳糖半乳糖化为GalNAcalpha-OC_6 H_4 NO_2-p，制备Galbeta 1 - 3 GalNAcalpha-OC_6 H_4 NO_2-p（2）。所得2通过东方诺卡氏菌beta-N-乙酰己糖胺酶介导的糖基转移作用转化为目标化合物1。N-乙酰氨基葡萄糖三糖（3 '-O-β-N-乙酰氨基葡萄糖-N-乙酰乳糖胺糖苷，简称3，GlcNAcbeta 1 - 3Galbeta 1 -4GlcNAcbeta-OC_6 H_4 NO_2-p）是聚N-乙酰乳糖胺的共同三糖单元。在这种情况下，当使用对硝基苯基β-N-乙酰基乳糖胺受体与α-环糊精的包合复合物时，糖苷酶介导的所需三糖糖苷（3）的形成的区域选择性基本上改变。利用N-乙酰氨基乳糖及其相关化合物合成人工糖共聚物。本文合成了两种主链为聚丙烯酸链和聚谷氨酸肽链的糖共聚物，并将其作为寡糖选择性分析的模型。这些水溶性糖聚合物与相应的凝集素发生特异性相互作用，无论聚合物中有多少个侧链是短链的，如二糖单元。