A series of monosaccharide (46), disaccharide (3,712), and trisaccharide (1315) analogs of the native ligand 2, which fills the binding site of monoclonal antibody Se 155.4, have been synthesized and their bioactivity measured by solid- and solution-phase assays. The syntheses of disaccharide analogs sought to replace galactose by various alkyl groups at the O-2 position of mannose. The activity of one of these O-2 alkyl analogs was 75% of that observed for the trisaccharide and points to only weak net bonding between the solvent exposed galactose residue and the antibody binding site. The synthesis of talose analogs 13 and 14, where the mannose or galactose residues of 2 were replaced by talose produced ligands with activities from one-third to one-half of that seen for the native ligand 2. These activity changes did not exhibit discernable correlations with the ability of talose to disrupt water of solvation.Key words: abequose, 3,6-dideoxy-D-xylo-hexose, talose disaccharide and trisaccharide, antibody oligosaccharide interactions, molecular recognition of carbohydrates, water in antibody complexes, Salmonella LPS, monoclonal antibody Se 155.4, bacterial O-antigen.
一系列
单糖(4-6)、二糖(3、7-12)和三糖(13-15)类似物已经合成,它们是原生
配体2的类似物,填充了单克隆
抗体Se 155.4的结合位点,并通过固相和溶液相测定了它们的
生物活性。二
糖类似物的合成旨在将半
乳糖替换为
甘露糖的O-2位置的各种烷基。其中一种O-2烷基类似物的活性为观察到的三糖活性的75%,表明溶剂暴露的半
乳糖残基与
抗体结合位点之间只有弱的净键合。通过将原生
配体2的
甘露糖残基替换为
甜菜糖合成了甜菜
糖类似物13和14,这些
配体的活性为原生
配体2的三分之一到一半。这些活性变化与
甜菜糖破坏溶剂
水的能力之间没有明显的相关性。关键词:阿贝酮,3,6-二去氧-
D-木糖-己糖,
甜菜糖二糖和三糖,
抗体寡糖相互作用,
碳水化合物的分子识别,
抗体复合物中的
水,沙门氏菌LPS,单克隆
抗体Se 155.4,细菌O抗原。