16497-92-0Relevant academic research and scientific papers
Dissociative electron transfer to and from pyrimidine cyclobutane dimers: an electrochemical study.
Boussicault, Fabien,Krueger, Oliver,Robert, Marc,Wille, Uta
, p. 2742 - 2750 (2004)
Cyclic voltammetry was used to study the reduction and oxidation behaviour of several pyrimidine cyclobutane dimers mimicking UV induced lesion in DNA strands in polar solvents (N,N-dimethylformamide and acetonitrile). Both electron injection and removal to and from the dimers, respectively, lead to their cleavage and reformation of the monomeric base. The influence of stereochemistry and substitution pattern at the cyclobutane motif on the reactivity has been studied. It appears that the repair process always proceeds in a sequential fashion with initial formation of a dimer ion radical intermediate, which then undergoes ring opening by homolytic cleavage of the two C-C bonds. Standard redox potentials for the formation of both radical anion and radical cation state of the dimers were determined. Quantum calculations on simplified model compounds reveal the reason for the finding that the exergonic homolytic cleavages of the carbon-carbon bonds are endowed with sizeable activation barriers. The consequences of these mechanistic studies on the natural enzymatic repair by photolyase enzyme are discussed. Copyright 2004 The Royal Society of Chemistry
HIGHLY STEREOSELECTIVE PHOTODIMERIZATION OF 1,3-DIMETHYLTHYMINE IN LIQUID CRYSTALLINE MEDIA
Kunieda, Takehisa,Takahashi, Toshie,Hirobe, Masaaki
, p. 5107 - 5108 (2007/10/02)
Ordered media such as cholesteric and smectic solvents greatly enhance the stereoselectivity and the rate in photodimerization of 1,3-dimethylthymine, in contrast to the isotropic phase reactions leading to a poor product-selectivity.
