An efficient PyAOP-based C-4-amination method for direct access of oxidized (5Me)dC derivatives

作者：Zheng, Xiu-An; Huang, Hua-Shan; Kong, Rui; Chen, Wei-Jie; Gong, Shan-Shan^*; Sun, Qi^*

来源：Tetrahedron, 2018, 74(49): 7095-7101.

DOI：10.1016/j.tet.2018.10.046

• PyAOP
• Amination
• Activation
• Aminolysis
• 5-Methyl-2 '-deoxycytidine

In the past decade, synthetic oxidized (5-Me)dC nucleosides and their derivatives have become essential tools for epigenetic research. The low efficacy of both conventional and newly reported BOP methods on C-4-amination of these specific oxidized (5-Me)dU substrates urged us to systematically investigate how the nature of onium salt-based coupling reagents affects the C-4-amination of pyrimidine nucleobases and lead us to the findings that different onium coupling reagents result in the formation of distinctive activation intermediates and PyAOP is much more potent than BOP in both activation and aminolysis steps. Direct amination without the need of ribose protection, ultrafast activation, tolerance to aqueous N-nucleophiles, and excellent yields for diverse oxidized (5Me)dC derivatives are the advantages of this PyAOP-based C-4-amination method. 2018 Elsevier Ltd.

• 出版日期2018-12-6
• 单位江西科技师范大学