Site-specific introduction of (5'S)-5', 8-cyclo-2'-deoxyadenosine into oligodeoxyribonucleotides

A Romieu, D Gasparutto, D Molko…

Index: Romieu, Anthony; Gasparutto, Didier; Molko, Didier; Cadet, Jean Journal of Organic Chemistry, 1998 , vol. 63, # 15 p. 5245 - 5249

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Citation Number: 79

Abstract

5′, 8-Cyclo-2′-deoxyadenosine (CyclodAdo) is one of the main radiation-induced decomposition products of 2′-deoxyadenosine (dAdo). 1 The formation of CyclodAdo is explained in terms of intramolecular attack of the C-8, N-7 double bond of the purine base by the C-5′ carbon radical, produced by the action of• OH radicals formed by the radiolysis of water. 2 The reaction is highly stereoselective since only the (5′ R)-diastereomer 1 is ...