Novel synthesis of nucleoside 5'-phosphoramidates through reaction of nucleoside triphosphates with amines mediated by trimethylsilyl chloride.
Reaction of nucleoside triphosphates (NTPs) with amines in pyridine mediated by trimethylsilyl chloride produced nucleoside 5'-phosphoramidates in moderate yields without any preprotection of nucleosides and amino acid methyl esters. The reaction pathway is very similar to the mechanism of the RNA capping reaction, DNA or RNA ligation reaction, and catalysis of hydrolases and nucleases involving the formation of covalent enzyme-NMP (nucleoside 5'-monophosphate) intermediates in biological systems, which could provide a valuable clue for the enzymatic reactions.
Zhu
Jigang
J
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
Han
Bo
B
Fu
Hua
H
Jiang
Yuyang
Y
Zhao
Yufen
Y
D000588:Amines / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000588:Amines; D009711:Nucleotides; D009943:Organophosphorus Compounds; D011725:Pyridines; D014297:Trimethylsilyl Compounds; C023666:pyridine