Preparation of Carbohydrate Polymers Containing Three Different Tumor-Associated Carbohydrate Antigens

• Main Authors: LIU, SI-XIAN, 劉思嫺
• Other Authors: CHANG, CHE-CHIEN
• Format: Others
• Language: zh-TW
• Published: 2019
• Online Access: http://ndltd.ncl.edu.tw/handle/2sgct7

碩士 === 輔仁大學 === 化學系 === 107 === Preparation of styrene-type glycoconjugates monomers, containing tumor-associated carbohydrate antigens (TACAs), such as Tn (Ser- / Thr- type), TF and sTn were developed. Polymerization of these TACAs monomers with polystyrene framework by NMP (Nitroxide-mediated radical polymerization) were also studied. Tn antigens were synthesized by the glycosylation reactions of D-galactose derivative, as glycol donor and L-serine or L-threonine derivatives as glycol acceptors. The first glycosylation reaction was proceeded to get the glycoproteins building blocks. The α-anomer was separated, and then attached to styrene through a spacer of diethylene glycol amine. The Tn glycoconjugate monomers were polymerized successfully to afford Tn glycoconjugate glycopolymers. To prepare others antigens, several functional groups were protected. Attachments of the second carbohydrate moieties, such as D-galatose and sialic acid, were constructed by the second glycosylation reactions. These two antigens were synthesized by the same methods used in the synthesis of Tn monomers, and eventually afforded three different types of glycoconjugates monomers. Controlled living radical polymerization (CLRP) of these three Tn glycoconjugate monomers were studied to produce the random and block co-polymers. Resulting glycopolymers were analyzed by NMR and ATR-IR to confirm TACAs presented on the polystyrene backbone.