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Nucleic Acids Research, 1988, Vol. 16, No. 11 5123-5136
© 1988

Articles

Synthesis of a trans-syn thymine dimer building block. Solid phase synthesis of CGTAT[t,s]TATGC

John-Stephen Taylor and Ian R. Brockie

Department of Chemistry, Washington University St Louis, MO 63130, USA

*To whom correspondence should be addressed

Received January 26, 1988. Revised May 6, 1988. Accepted May 6, 1988.

The synthesis of a building block for the sequence specific introduction of the trans-syn thymine dimer into oligonucleotides via solid phase DNA synthesis technology is described. CGTAT[t,s]TATGC was synthesized in 48% overall yield by a partially automated procedure. The stepwise coupling yield for addition of the trans-syn thymine dlmer building block was 58%. The dimer containing oligonucleotlde was characterized by 500 MHz 1H COSY and NOESY spectroscopy and 202.5 MHz 31P NMR. The 1H chemical shifts for the trans-syn thymine dimer unit of the decamer were found to be quite similar to those found for the trans-syn thymine dimer of TpT. Upon photolysis at 254 tin, CGTAT[t,s]TATGC was converted to a major product which coeluted with authentic CGTATTATGC and a minor product which coeluted with authentic CGTAT[c,s]TATGC, further supporting the presence of an intact trans-syn thymine dimer unit.


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