410096-52-5Relevant academic research and scientific papers
Stereodefined synthesis of O3′-labeled uracil nucleosides. 3′-[17O]-2′-azido-2′-deoxyuridine 5′-diphosphate as a probe for the mechanism of inactivation of ribonucleotide reductases
Wnuk, Stanislaw F.,Chowdhury, Saiful M.,Garcia Jr., Pedro I.,Robins, Morris J.
, p. 1816 - 1819 (2002)
Thermolysis of a 2′-[16O]-O-benzoyl-[17O]-5′-O-(tert- butyldimethylsilyl)-O2,3′-cyclouridine derivative gave the more stable 3′-[17O]-O-benzoyl-[16O]-5′-O-(tert- butyldimethylsilyl)-O2,2′-cyclouridine isomer, which was converted into 3′-[17O]-2′-azido-2′-deoxyuridine by deprotection and nucleophilic ring opening at C2′ with lithium azide. The 5′-diphosphate was prepared by nucleophilic displacement of the 5′-O-tosyl group with tris(tetrabutylammonium) hydrogen pyrophosphate. Model reactions gave 16O and 18O isotopomers, and base-promoted hydrolysis of an O2,2′-cyclonucleoside gave stereodefined access to 3′-[18O]-1-(β-D-arabinofuranosyl)uracil. Inactivation of ribonucleoside diphosphate reductase with 2′-azido-2′-deoxynucleotides results in appearance of EPR signals for a nitrogen-centered radical derived from azide, and 3′-[17O]-2′-azido-2′-deoxyuridine 5′-diphosphate provides an isotopomer to perturb EPR spectra in a predictable manner.
