Preparation of Glycopolymers Containing Tumor-associated Carbohydrate Antigens by Nitroxide-Mediated Polymerization

• Main Authors: TSAI, YUN-TZU, 蔡芸慈
• Other Authors: CHANG, CHE-CHIEN
• Format: Others
• Language: zh-TW
• Published: 2018
• Online Access: http://ndltd.ncl.edu.tw/handle/d54gk9

碩士 === 輔仁大學 === 化學系 === 106 === Starting from D-galactose, the glycosyl donor was prepared within 4 steps. In contrast, the glycosyl acceptor consisting of diethylene glycol and styrene to carry out the glycosylation reaction. After the product is obtained, the azide group is converted into an NHAc group to obtain a glycolmonomer, and a different sugar ratio polymer is prepared by using the NMP polymerization. On the other hand, in order to synthesize a product that is closer to a authentic structures of Tn antigens, benzyl group was first protected by Fmoc-Ser- OH as an starting material on the carboxylic acid, followed by the glycosylation reaction with a glycosyl donor, then coupled with a spacer to obtain a Tn-containing glycolmonomer for polymerization. From the experimental results, it is inferred that the Fmoc protecting group may be cleaved at a high temperature for a long time, causing difficulty in the polymerization reaction. In order to improve this situation, we converted its protecting group to acetyl group to obtain a sugar monomer for NMP reaction. Currently, all glycolpolymers can be confirmed by 1H NMR and IR spectra. This study provides the first synthesis method for the preparation of Tn glycolmonomer, and is the first ever to produce Tn-containing glycolmonomer by NMP reaction.