Issue 9, 2011

Radical-based alkylation of guanine derivatives in aqueous medium

Abstract

The radical-based alkylation of 8-bromoguanosine (1a) and 8-bromo-2′-deoxyguanosine (1b) at the C8 position has been investigated in aqueous solutions. Alkyl radicals were generated by scavenging of the primary species of γ-radiolysis by the alcohol substrate. These reactions result in the efficient formation of intermolecular C–C bonds in aqueous media, by using the reactivity of α-hydroxyalkyl radicals derived from alcohols with 1a and 1b. A mechanism for the formation of C8 guanine alkylated adducts has been proposed, based on the quantification of radiation chemical yields for the disappearance of starting material and the formation of all products. Two α-hydroxyalkyl radicals are needed to form an alkylated guanine, the first one adding to C8 followed by ejection of Br with formation of guanyl adduct and the second one acting as reducing agent of the guanyl adduct.

Graphical abstract: Radical-based alkylation of guanine derivatives in aqueous medium

Article information

Article type
Paper
Submitted
28 Dec 2010
Accepted
22 Feb 2011
First published
24 Mar 2011

Org. Biomol. Chem., 2011,9, 3494-3498

Radical-based alkylation of guanine derivatives in aqueous medium

C. Chatgilialoglu, C. Caminal and Q. G. Mulazzani, Org. Biomol. Chem., 2011, 9, 3494 DOI: 10.1039/C0OB01264E

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