Reaction of Br3 ·2- with 2-Deoxy-D-ribose. A Preferred Attack at C-1
Open Access
- 1 June 1978
- journal article
- research article
- Published by Walter de Gruyter GmbH in Zeitschrift für Naturforschung B
- Vol. 33 (6) , 666-668
- https://doi.org/10.1515/znb-1978-0622
Abstract
In the photolysis of 5-bromouracil containing DNA Br atoms are expected intermediates. In order to evaluate the possible site of attack of the Br atom at the sugar moiety of DNA the reaction of 2-deoxy-D-ribose with the Br atom (complexed with 2 bromide ions) was investigated. Hydroxyl radicals generated by the radiolysis of N2O saturated aqueous solutions were converted into Br3.2- radicals by 1 M bromide ions. Br3.2- reacts with 2-deoxy-D-ribose (k = 3.7 .cntdot. 104 M-1 s-1, pulse radiolysis). The major product is 2-deoxy-D-erythro-pentonic acid (G = 2.4, .gamma.-radiolysis). It is formed by H abstraction from C-1 and oxidation of this radical by other radicals. An alternative route via the radical at C-2 is neglible. It follows that Br3.2- reacts preferentially at C-1 of 2-deoxy-D-ribose.This publication has 3 references indexed in Scilit:
- γ-Radiolyses of DNA in Oxygenated Aqueous Solution. Structure of an Alkali-Labile SiteZeitschrift für Naturforschung C, 1977
- Isolation of 2-deoxy-d-erythro-pentonic Acid from an Alkali-labile Site in γ-irradiated DNAInternational Journal of Radiation Biology and Related Studies in Physics, Chemistry and Medicine, 1977
- Search for a mechanism for the increased sensitivity of 5-bromouracil-substituted DNA to ultraviolet radiationBiochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis, 1968