CYCLIZATION BY FREE-RADICAL ADDITION OF STANNYL OR THIYL RADICAL TO 3'-BETA-ETHYNYL URIDINE - IS THE 3'-BETA-ETHYNYL GROUP-A SPIN TRAP IN RIBONUCLEOTIDE REDUCTASE

Authors
JUNG PMJ DAUVERGNE J BURGER A BIELLMANN JF
Citation
Pmj. Jung et al., CYCLIZATION BY FREE-RADICAL ADDITION OF STANNYL OR THIYL RADICAL TO 3'-BETA-ETHYNYL URIDINE - IS THE 3'-BETA-ETHYNYL GROUP-A SPIN TRAP IN RIBONUCLEOTIDE REDUCTASE, Tetrahedron letters, 38(33), 1997, pp. 5877-5880
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
33
Year of publication
1997
Pages
5877 - 5880
Database
ISI
SICI code
0040-4039(1997)38:33<5877:CBFAOS>2.0.ZU;2-Q
Abstract
Reaction of a stannyl or a thiyl radical, generated in situ with AIBN, on thylsilyl-3'-C-ethynyl-beta-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'-beta-ethynyl uridine di-and triph osphates could be a spin trap of the transient thiyl radical of ribonu cleotide reductases. (C) 1997 Elsevier Science Ltd.