Blocking cyclobutane pyrimidine dimer formation by steric hindrance

The efficiency of thymine (Thy) and uracil (Ura) to form cyclobutane pyrimidine dimers (CPDs) in solution, upon UV irradiation differs by one order of magnitude. This could to be partially related to the steric hindrance induced by the methyl at C5 in thymine. The aim of the present work is to estab...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (17), p.411-4115
Main Authors: Vendrell-Criado, Victoria, Lhiaubet-Vallet, Virginie, Yamaji, Minoru, Cuquerella, M. Consuelo, Miranda, Miguel A
Format: Article
Language:English
Subjects:
Acetone - chemistry
Benzophenones - chemistry
Cyclobutanes - chemistry
Dimerization
Lasers
Molecular Structure
Photolysis
Photosensitizing Agents - chemistry
Pyrimidine Dimers - chemical synthesis
Pyrimidine Dimers - chemistry
Ultraviolet Rays
Uracil - analogs & derivatives
Uracil - chemistry
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Summary:The efficiency of thymine (Thy) and uracil (Ura) to form cyclobutane pyrimidine dimers (CPDs) in solution, upon UV irradiation differs by one order of magnitude. This could to be partially related to the steric hindrance induced by the methyl at C5 in thymine. The aim of the present work is to establish the influence of a bulky moiety at this position on the photoreactivity of pyrimidines. With this purpose, photosensitization with benzophenone and acetone of a 5- tert -butyl uracil derivative ( 1 ) and the equivalent Thy ( 2 ) has been compared. Introduction of the tert -butyl group completely blocks CPD formation. Moreover, the mechanistic insight obtained by laser flash photolysis is in accordance with the observed photoreactivity. Replacement of the C5 thymine methyl group with a bulky tert-butyl substituent completely blocks the formation of CPDs.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob00382f