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Efficient Synthesis of [2‘- 18 O]Uridine and Its Incorporation into Oligonucleotides: A New Tool for Mechanistic Study of Nucleotidyl Transfer Reactions by Isotope Effect Analysis

2007; American Chemical Society; Volume: 73; Issue: 1 Linguagem: Inglês

10.1021/jo701727h

1520-6904

Qing Dai, John K. Frederiksen, Vernon Anderson, Michael E. Harris, Joseph A. Piccirilli,

DNA and Nucleic Acid Chemistry

Lack of sufficient quantities of isotopically labeled materials has precluded the use of heavy atom isotope effects to investigate mechanisms of nucleotidyl transfer reactions in nucleic acids. Here we achieve regioselective opening of 2,2'-cyclouridine with [(18)O2]benzoic acid/potassium hydride, allowing an efficient "one-pot" synthesis of [2'-18O]uridine in 88% yield. Conversion to the corresponding phosphoramidite enables solid-phase synthesis of [2'-(18)O] RNA substrates for isotope effect studies with nucleotidyl transferases and hydrolases.