- 學位論文
含硼化合物的合成以及其醣類結合能力的評估
Synthesis of Boron-containing Analogs and the Evaluation of their Saccharide Binding Ability
摘要
硼酸由於能與唾液酸的α- hydroxyacid和甘油鏈產生鍵結，所以常當作識別唾液酸探針使用。本論文提出利用方便且有效率的 Ugi 多組成反應 ( Scheme 1 )，合成出一系列不同位點的雙硼酸結構，藉由硼酸位點的不同，尋找出有利於唾液酸結合的結構。 透過雙硼酸Ugi結構的研究，揭示了與唾液酸的結合具有一定的順序性。當唾液酸與雙硼酸 Ugi 結構胺端形成鍵結時，產生的氫鍵作用力可能引發誘導效應，有助於原先未鍵結的硼酸與唾液酸的結合。為了驗證這一推測，衍生出最佳的雙硼酸 Ugi 結構 B5 ( Figure 1 )，其結合常數高達7015 M-1，相較於之前最佳 B1 結構的結合常數高出2.5倍。
並列摘要
Boronic acid is often used as a probe for identifying sialic acid because it can bond with α-hydroxyacid and glycerol chains of sialic acid. This paper proposes to use the convenient and efficient Ugi multi-composition reaction (Scheme 1) to synthesize a series of diboronic acid structures with different positions, and to find structures that are conducive to sialic acid binding through the differences in the boronic acid positions. The Ugi structure of bisboronic acid speculates that when sialic acid forms a bond with the amine end of the Ugi structure of bisboronic acid, the resulting hydrogen bond force may induce an inductive effect, which is conducive to the combination of unbonded boric acid and sialic acid ( Figure 2 ). In order to verify this speculation, the best bisboronic acid Ugi structure was derived, and its binding constant was as high as 7015 M-1, which was 2.5 times higher than that of the previous structure.