Organic Letters, volume 12, issue 18, pages 4130-4133

Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

R. Amorati ¹

Luca Valgimigli ¹

Gian Franco Pedulli ¹

Stanislav A. Grabovskiy ¹

Natalia N. Kabal'nova ¹

Chryssostomos Chatgilialoglu ¹

Department of Organic Chemistry “A. Mangini”, University of Bologna, Via S. Giacomo 11, I-40126 Bologna, Italy, and ISOF, Consiglio Nazionale delle Ricerche, Via P. Gobbetti 101, I-40129 Bologna, Italy |

Publication type: Journal Article

Publication date: 2010-08-26

American Chemical Society (ACS)

Journal: Organic Letters

scimago Q1

SJR: 1.245

CiteScore: 9.3

Impact factor: 4.9

ISSN: 15237060, 15237052

DOI: 10.1021/ol1017245

Copy DOI

PubMed ID: 20795653

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Addition of millimolar amounts of a weak base (pyridines) dramatically accelerates the reaction with peroxyl radicals of two biologically relevant uracil derivatives, 5-hydroxyuracil (HU) and 5-hydroxy-6-methyluracil (HMU). This is due to the formation of small amounts of the deprotonated form (pK(a) = 8.1-8.5 in water), which reacts with peroxyl radicals much faster than the parent undissociated form, via formal H-atom transfer from the OH in the 5 position.

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Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

SJR

1.245

CiteScore

9.3

Impact factor

4.9

ISSN

15237060 (Print)

15237052 (Electronic)

Profiles

Grabovskiy, Stanislav A

Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

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