N,S-桥连硫代磷酰胺酯类似物的合成、构象和水解稳定性。
The synthesis, conformation and hydrolytic stability of an N,S-bridging thiophosphoramidate analogue of thymidylyl-3',5'-thymidine.
机构信息
Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK.
Department of Chemistry, University of Turku, Vatselankatu 2, 20014 Turku, Finland.
出版信息
Org Biomol Chem. 2016 Jul 26;14(30):7361-7. doi: 10.1039/c6ob01270a.
A 3'-N,5'-S-bridging thiophosphoramidate analogue of thymidylyl-3',5'-thymidine was synthesised under aqueous conditions. (1)H NMR conformational measurements show that the 3'-N-substituted deoxyribose ring is biased towards the 'north', RNA-like conformation. Rate constants for hydrolysis of the analogue were measured at 90 °C in the pH range 1.3-10.9. The pH-log kobs profile displays a pH-independent region between approximately pH 7 and 10 (t1/2 ∼13 days). Under acidic conditions, kobs displays a first order dependence on [H3O(+)].
在水相条件下合成了 3'-N，5'-S-桥连硫代磷酰胺基胸苷类似物。（1）H NMR 构象测量表明，3'-N 取代的脱氧核糖环偏向“北”，类似于 RNA 的构象。在 90°C 下，在 pH 值为 1.3-10.9 的范围内测量了类似物的水解速率常数。pH-log kobs 曲线在大约 pH 7 到 10 之间呈现 pH 独立区域（t1/2∼13 天）。在酸性条件下，kobs 对[H3O（+）]呈一级依赖关系。
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