Synthesis of Biocompatible Materials Having Blood-Group Antigenic 01 igosaccharide Chain

具有血型抗原01寡糖链的生物相容性材料的合成

• 批准号: 02650662
• 负责人: HATANAKA Kenichi
• 金额: $ 1.54万
• 依托单位: Tokyo Institute of Technology
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1990
• 资助国家: 日本
• 起止时间: 1990 至 1992
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-02650662/
• 关键词: Blood group; Biomaterial; Oligosaccharide; Glycosyl transferase; Debenzylation; Polymer material; Orthoester glycosylation; 生体認識; 血液型抗原; オリゴ糖; 高分子材料; 生体適合性; 糖転移酵素; ABO式血液型; 合成高分子; 酵素; H型抗原; オリゴ糖鎖; 共重合; 糖転移; HI型糖鎖; 抗原決定基; オリゴ糖モノマ-

A new polymerizable monomer having a nonreducing-terminal trisaccharide of an H type antigenic oligosaccharide was synthesized chemically, that is, 5-(2-acryloyloxyethylaminocarbonyl)pentyl 2-acetamido-4,6-0-benzylidene-2-deoxy-3-0-[3,4,6-tri-0-benzyl-2-0-(2,3,4- tri-0-benzyl-alpha-L-fucopyranosyl)-beta-D-galactopyranosyl]-beta-D-glucopyranoside, and was copolymerized with acrylamide or methyl acrylate. Copolymerization of the synthetic sugar monomer with acrylamide was carried out in dimethylformamide with AIBN as initiator, and copolymerization with methyl acrylate was carried out in benzene with the same initiator. The copolymer composition which was calculated by ^1H-NMR spectroscopy was controlled by the monomer ratio in the feed. The monomeric unit having an H type antigenic oligosaccharide was introduced into the copolymer in a content of 0.005 to 0.54. The number average molecular weight of the copolymer was in the range of 1.8 X 10^4 to 8.4 X 10^4. Benzyl and benzylidene groups, which were the protective groups of the copolymers, were removed by catalytic hydrogenation over palladium-carbon in the mixed solvent of DMF-H_2O. Transfer of N-acetyl-D-galactosamine to the galactose residue in the copolymer by using A enzyme (GalNAc transferase) was attempted, showing the transfer of GalNAc residue.

化学合成了一种新的H型抗原寡糖非还原端三糖可聚合单体，即5-(2-丙烯酰氧基乙基氨基羰基)戊基2-乙酰氨基-4,6-0-亚苄基-2-脱氧-3-0 -[3,4,6-三-0-苄基-2-0-(2,3,4-三-0-苄基-α-L-吡喃岩藻糖基)-β-D-吡喃半乳糖基]-β-D-吡喃葡萄糖苷，与丙烯酰胺或丙烯酸甲酯共​​聚。合成糖单体与丙烯酰胺在二甲基甲酰胺中以AIBN为引发剂进行共聚，与丙烯酸甲酯在苯中以相同引发剂进行共聚。通过 1 H-NMR光谱计算的共聚物组成由进料中的单体比例控制。具有H型抗原性寡糖的单体单元以0.005至0.54的含量引入到共聚物中。该共聚物的数均分子量在1.8×10^4至8.4×10^4的范围内。在DMF-H_2O混合溶剂中，通过钯-碳催化加氢去除了共聚物的保护基苄基和亚苄基。尝试使用A酶(GalNAc转移酶)将N-乙酰基-D-半乳糖胺转移至共聚物中的半乳糖残基，显示GalNAc残基的转移。