Synthesis of a trans-syn thymine dimer building block. Solid phase synthesis of CGTAT[t,s]TATGC.
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 dimer building block was 58%. The dimer containing oligonucleotide 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 nm, 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.
Taylor
J S
JS
Department of Chemistry, Washington University, St Louis, MO 63130.
Brockie
I R
IR
D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010777:Photochemistry; D011740:Pyrimidine Dimers / Q000138:chemical synthesis
D011740:Pyrimidine Dimers