Encapsulation of Vitamin B1 and Its Phosphate Derivatives by Cucurbit[7]uril: Tunability of the Binding Site and Affinity by the Presence of Phosphate Groups

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• 作者：Shengke Li ; Hang Yin ; Ian W. Wyman ; Qingwen Zhang ; Donal H. Macartney ; Ruibing Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：81
• 期：3
• 页码：1300-1303
• 全文大小：352K
• ISSN：1520-6904

文摘

Vitamin B₁ (1) and its phosphate derivatives, thiamine monophosphate (2) and thiamine pyrophosphate (3), are shown to form stable 1:1 host–guest complexes with cucurbit[7]uril (CB[7]) in aqueous solution. The binding sites of CB[7] on these guests shift from the ethylthiazolium region of 1 to the pyrimidine moiety of 2 and 3 due to the presence of phosphate groups, leading to variations of binding affinities as well as C(2)–H/D exchange rate constants and C(2)–H pK_a values with these guest molecules.