Kaifu R, Osawa T, Jeanloz R W
Carbohydr Res. 1975 Mar;40(1):111-7. doi: 10.1016/s0008-6215(00)82673-7.
Condensation of 3, 4:5, 6-di-O-isopropylidene-D-mannose dimethyl acetal with 2-methyl-(3, 4, 6-tri-O-acetyl-1, 2-dideoxy-alpha-D-glucopyrano)-[2', 1':4, 5]-2- oxazoline in the presence of a catalytic amount of p-toluenesulfonic acid afforded crystalline 2-O-(2-acetamido-3, 4, 6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-3, 4:5, 6-di-O-isopropylidene-D-mannose dimethyl acetal (3) in 25 percent yield. Catalytic deacetylation of 3 with sodium methoxide, followed by hydrolysis with dilute sulfuric acid, gave 2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-D-mannose (4). Treatment of 3 with boiling 0.5 percent methanolic hydrogen chloride under reflux gave methyl 2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D-mannopyranoside (5) and methyl 2-o-2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D-mannofuranoside (6). The inhibitoryactivities of 4, 5, and 6 against the hemagglutinating and mitogenic activities of Lens culinaris and Pisum sativum lectins and concanavalin A were assayed. From the results of these hapten inhibition studies, subtle differences of specificity between these D-mannose-specific lectins were confirmed.
在催化量的对甲苯磺酸存在下，使3,4:5,6 - 二 - O - 异亚丙基 - D - 甘露糖二甲基缩醛与2 - 甲基 - (3,4,6 - 三 - O - 乙酰基 - 1,2 - 二脱氧 - α - D - 吡喃葡萄糖基)-[2',1':4,5]-2 - 恶唑啉缩合，得到结晶状的2 - O - (2 - 乙酰氨基 - 3,4,6 - 三 - O - 乙酰基 - 2 - 脱氧 - β - D - 吡喃葡萄糖基)-3,4:5,6 - 二 - O - 异亚丙基 - D - 甘露糖二甲基缩醛（3），产率为25%。用甲醇钠对3进行催化脱乙酰化，然后用稀硫酸水解，得到2 - O - (2 - 乙酰氨基 - 2 - 脱氧 - α - D - 吡喃葡萄糖基)-D - 甘露糖（4）。在回流条件下，用沸腾的0.5%甲醇盐酸处理3，得到甲基2 - O - (2 - 乙酰氨基 - 2 - 脱氧 - β - D - 吡喃葡萄糖基)-α - D - 甘露吡喃糖苷（5）和甲基2 - O - (2 - 乙酰氨基 - 2 - 脱氧 - β - D - 吡喃葡萄糖基)-α - D - 甘露呋喃糖苷（6）。测定了4、5和6对小扁豆和豌豆凝集素以及伴刀豆球蛋白A的血凝活性和促有丝分裂活性 的抑制活性。从这些半抗原抑制研究的结果中，证实了这些D - 甘露糖特异性凝集素之间特异性的细微差异。
