Ma Xingquan, Saksena Rina, Chernyak Anatoly, Kovác Pavol
NIDDK, LMC, National Institutes of Health, Bethesda, MD 20892, USA.
Org Biomol Chem. 2003 Mar 7;1(5):775-84. doi: 10.1039/b211660j.
A glycosyl acceptor and a glycosyl donor having the N-3-deoxy-L-glycero-tetronic acid side chain already attached have been prepared and used for the synthesis of the di-through to the hexasaccharide that mimic the upsteam terminus of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Inaba. The target tetra- and the hexasaccharide, which were obtained in the form of 5-methoxycarbonylpentyl glycosides, were linked to BSA using squaric acid diester chemistry. The conjugation reactions were monitored by surface enhanced laser desorption ionization-time of flight mass spectrometry (SELDI-TOF MS). This allowed the progression of the conjugation of the synthetic oligosaccharides in a controlled way and termination of the reaction when the desired molar hapten/BSA ratio had been reached, yielding neoglycoconjugates with predetermined carbohydrate/carrier ratios. The ability to monitor the conjugation by the SELDI-TOF MS technique made it possible to prepare, from one hapten in a one-pot reaction, several neoglycoconjugates having different, predetermined carbohydrate/carrier ratios.
已经制备了具有已连接的N-3-脱氧-L-甘油四糖酸侧链的糖基受体和糖基供体，并将其用于合成二糖至六糖，这些糖模拟霍乱弧菌O:1稻叶血清型O-特异性多糖的上游末端。以5-甲氧基羰基戊基糖苷形式获得的目标四糖和六糖，使用方酸二酯化学方法与牛血清白蛋白（BSA）连接。通过表面增强激光解吸电离飞行时间质谱（SELDI-TOF MS）监测偶联反应。这使得合成寡糖的偶联反应能够以可控的方式进行，并在达到所需的摩尔半抗原/BSA比率时终止反应，从而产生具有预定碳水化合物/载体比率的新糖缀合物。通过SELDI-TOF MS技术监测偶联反应的能力使得在一锅反应中从一种半抗原制备几种具有不同预定碳水化合物/载体比率的新糖缀合物成为可能。
