Tetrahedron Letters

The reaction of activated RNA species with aqueous fluoride ion: a convenient synthesis of nucleotide 5′-phosphorofluoridates and a note on the mechanism

MF Aldersley, PC Joshi, HM Schwartz, AJ Kirby

Index: Aldersley, Michael F.; Joshi, Prakash C.; Schwartz, Herbert M.; Kirby, Anthony J. Tetrahedron Letters, 2014 , vol. 55, # 8 p. 1464 - 1466

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Citation Number: 5

Abstract

Abstract The chemistry of 5′-phosphorimidazolides of ribonucleosides is extended to include their reaction with alkali metal fluorides in aqueous solution. High yields of 5′- phosphorofluoridates are formed, especially with potassium fluoride, but no detectable oligomerization products were formed. A combination of HPLC, mass spectrometry, synthesis, kinetics, and NMR confirms the identities of the products. Judicious control of ...