Párkányi L, Kálmán A, Czugler M, Kovács T, Walker R T
Nucleic Acids Res. 1987 May 26;15(10):4111-21. doi: 10.1093/nar/15.10.4111.
Crystal structures of (Z)-5-(2-bromovinyl)-2'-deoxyuridine, 3',5'-di-O-acetyl-(E)-5-(2-bromovinyl)-2'-deoxyuridine and 3',5'-di-O-p-chlorobenzoyl-5-(2-dibromovinyl)-2'-deoxyuridine are compared with each other and with that of the most potent antiviral agent (E)-5-(2-bromovinyl)-2'-deoxyuridine (E-BVDU) reported earlier. A comparison of the conformation of 3',5'-di-O-acetyl-pyrimidine nucleoside structures in which intermolecular hydrogen bond network formation is minimized, with those of their parent compounds has shown that the greatest change in rotation about the glycosyl bond and in the sugar ring pucker is exhibited by E-BVDU. Upon acylation this molecule changes from C2'-endo/C3'-exo conformation to C3'-endo/C4'-exo conformation. The relevance of these structures upon the biological activity of the nucleosides and in particular to their ability to be a substrate for thymidine kinase is discussed.
将（Z）-5-（2-溴乙烯基）-2'-脱氧尿苷、3'，5'-二-O-乙酰基-（E）-5-（2-溴乙烯基）-2'-脱氧尿苷和3'，5'-二-O-对氯苯甲酰基-5-（2-二溴乙烯基）-2'-脱氧尿苷的晶体结构相互之间以及与先前报道的最有效的抗病毒剂（E）-5-（2-溴乙烯基）-2'-脱氧尿苷（E-BVDU）的晶体结构进行比较。对分子间氢键网络形成最小化的3'，5'-二-O-乙酰基嘧啶核苷结构与其母体化合物的构象进行比较表明，E-BVDU在糖苷键旋转和糖环构象方面表现出最大变化。酰化后，该分子从C2'-内型/C3'-外型构象转变为C3'-内型/C4'-外型构象。讨论了这些结构与核苷生物活性的相关性，特别是与它们作为胸苷激酶底物的能力的相关性。
