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Published online 12 March 2004

Nucleic Acids Research, 2004, Vol. 32, No. 5 1738-1745
© 2004 Oxford University Press

Chemical synthesis and translesion replication of a cis–syn cyclobutane thymine–uracil dimer

Kohei Takasawa, Chikahide Masutani1,2, Fumio Hanaoka1,2 and Shigenori Iwai*

Division of Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan, 1 Graduate School of Frontier Biosciences, Osaka University and 2 Core Research for Evolutional Science and Technology, Japan Science and Technology Corporation, 1–3 Yamadaoka, Suita, Osaka 565-0871, Japan

*To whom correspondence should be addressed. Tel: +81 6 6850 6250; Fax: +81 6 6850 6240; Email: iwai{at}chem.es.osaka-u.ac.jp

The cytosine base in DNA undergoes hydrolytic deamination at a considerable rate when UV radiation induces formation of a cyclobutane pyrimidine dimer (CPD) with an adjacent pyrimidine base. We have synthesized a phosphoramidite building block of a cis–syn cyclobutane thymine–uracil dimer (T[]U), which is the deaminated form of the CPD at a TC site, and incorporated it into oligodeoxyribonucleotides. The previously reported method for synthesis of the thymine dimer (T[]T) was applied, using partially protected thymidylyl-(3'–5')-2'-deoxyuridine as the starting material, and after triplet- sensitized irradiation, the configuration of the base moiety in the major product was determined by NMR spectroscopy. Presence of the cis–syn cyclobutane dimer in the obtained oligonucleotides was confirmed by UV photoreversal and reaction with T4 endonuclease V. Using a 30mer containing T[]U, translesion synthesis by human DNA polymerase {eta} was analyzed. There was no difference in the results between the templates containing T[]T and T[]U and pol {eta} bypassed both lesions with the same efficiency, incorporating two adenylates. This enzyme showed fidelity to base pair formation, but this replication causes a C->T transition because the original sequence is TC.


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