Abstract: A new aldehyde-functionalized glycomonomer，1,2:3,4-Di-O-isopropylidene-6-O-(2’- formyl-4’-vinyl phenyl)-D-galactopyranose（IVDG），was designed and prepared by the reaction of 1,2:3,4-di-O-isopropylidene-6-O-(p-toluenesulfonyl)-D-galactopyranose（ITDG）with 2-hydroxy-5- vinylbenzaldehyde，and its structure was confirmed via elemental analysis，MS，and NMR spectroscopy. The radical polymerization of IVDG was successfully achieved using AIBN as initiator at 60 ℃ in THF. Removal of the protective isopropylidene group from the sugar residue in polyIVDG was carried out quantitatively using 88% formic acid at room temperature，yielding a novel polymer containing both galactopyranose and aldehyde functionalities. These amphiphilic polymers self-assembled into well-defined aldehydes-bearing polymeric micelles in aqueous solution without recourse to any surfactant. The hydrodynamic radius（Rh）of the micelles was 450nm by DLS in CONTIN algorithm. The micelles could be observed directly under TEM. The prepared nanospheres can potentially be applied in medicine and biotechnology.

摘要：

采用Witting等一系列化学反应合成了一种既含醛基又含糖基的乙烯基单体1,2∶3,4-Di-O-异亚丙基-6-O-（2’-甲醛-4’-苯乙烯基）-D-半乳糖（IVDG），该单体为白色粉末状，熔点为97～98 ℃，用元素分析、质谱和核磁分析进行了结构表征。在AIBN的引发下，60 ℃四氢呋喃中、24 h单体转化率可达到68%，聚合物相对分子质量为130000，表明该单体具有较高的聚合活性。经88%甲酸水解，脱去保护基团异亚丙基后，所得的聚合物具有两亲性，不需要外加乳化剂，在水中能够自组装形成含有大量醛基的纳米微球，动态光散射数据表明粒径为450 nm，其形貌可在透射电镜下直接观察。该聚合物在生物医药领域有潜在的应用前景。