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Cyclization by free radical addition of stannyl or thiyl radical to 3′-β-ethynyl uridine. Is the 3′-β-ethynyl group a spin trap in ribonucleotide reductase?

✍ Scribed by Pierre M.J Jung; Jérôme Dauvergne; Alain Burger; Jean-François Biellmann


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
235 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


Reaction of a stannyl or a thiyl radical, generated ~n situ with AIBN, on (2',5'-di-O-tertbmyldimethylsilyl-3'-C-ethynyl-{~-D-ribofuranosyl)uracil (2) gave in 60% and 17% yield respectively cyclized adducts 3 and 4 where the vinylic radical, formed by addition of stannyl or thiyl radical to the triple bond, reacted with the base. The 3'-~-ethynyl uridine di-and triphosphates could he a spin trap of the transient thiyl radical of ribonucleotide reductases.