Roy R, Tropper F D, Romanowska A, Letellier M, Cousineau L, Meunier S J, Boratyński J
Department of Chemistry, University of Ottawa, Ontario, Canada.
Glycoconj J. 1991 Apr;8(2):75-81. doi: 10.1007/BF00731015.
Starting from peracetylated chloro- or bromo-glycosyl donors of N-acetylneuraminic acid, N-acetylglucosamine, glucose and lactose, the corresponding p-formylphenyl glycosides were synthesized stereospecifically under phase transfer catalysed conditions at room temperature in yields of 38-67%. After Zemplén de-O-acetylation, the formyl groups were directly and chemoselectively coupled to the lysine residues of bovine serum albumin by reductive amination using sodium cyanoborohydride. The conjugation reactions were followed as a function of time and under a series of different molar ratios of the reactants to provide glycoconjugates of varying degree of antigenicities. Thus, carbohydrate protein conjugates were made readily available using essentially two key reactions.
从N-乙酰神经氨酸、N-乙酰葡糖胺、葡萄糖和乳糖的全乙酰化氯代或溴代糖基供体出发，在相转移催化条件下于室温立体定向合成相应的对甲酰基苯基糖苷，产率为38% - 67%。经泽普林脱O-乙酰化后，使用氰基硼氢化钠通过还原胺化将甲酰基直接且化学选择性地偶联至牛血清白蛋白的赖氨酸残基上。跟踪共轭反应随时间的变化情况，并在一系列不同反应物摩尔比下进行，以提供不同抗原性程度的糖缀合物。因此，通过基本上两个关键反应即可轻松制备碳水化合物 - 蛋白质缀合物。
