TY - JOUR
T1 - Synthesis of a trans-syn thymine dimer building block. Solid phase synthesis of CGTAT[t,s]TATGC
AU - Taylor, John Stephen
AU - Brockie, Ian R.
N1 - Funding Information:
This investigation was supported by PHS Grant number R01-CA40463, awarded by the National Cancer Institute, DHHS. The assistance of the Washington University High Resolution NMR Service Facility, funded in part through NIH Biomedical Research Support Shared Instrument Grant 1 S10 RR02004, and a gift from the Monsanto Company is gratefully acknowledged. We thank D. Garrett for the NMR spectrum of CGTATTATGC and D. Svoboda for the phosphorylating agent and a sample of CGTAT[c,s]TATGC. We thank Dr. Andrew Tyler for conducting fast atom bombardment mass spectrometry. Mass spectrometry data were obtained at the Washington University Mass Spectrometry Resource, which is supported by a grant from the NIH [RR00954].
PY - 1988/6/10
Y1 - 1988/6/10
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/0024283265
U2 - 10.1093/nar/16.11.5123
DO - 10.1093/nar/16.11.5123
M3 - Article
C2 - 3387219
AN - SCOPUS:0024283265
SN - 0305-1048
VL - 16
SP - 5123
EP - 5136
JO - Nucleic acids research
JF - Nucleic acids research
IS - 11
ER -