Stereoselective formation of a cyclobutane pyrimidine dimer by using N4-acetyl protection of the cytosine base.
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. As a part of our study on the synthesis of CPD-containing oligonucleotides, we have prepared properly-protected thymidylyl-(3' 5')-N(4)-acetyl-2'-deoxycytidine, and the solution of this compound was UV-irradiated using acetophenone as a sensitizer. In this reaction, hydrolysis of the acetylamino group occurred, and a trans-syn cyclobutane thymine-uracil dimer with the syn-anti conformation around the glycosidic bonds was formed stereoselectively.
Nishiguchi
Kosuke
K
Division of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan.
Yamamoto
Junpei
J
Iwai
Shigenori
S
D003503:Cyclobutanes / Q000737:chemistry*; D003596:Cytosine / Q000737:chemistry*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry; D011740:Pyrimidine Dimers / Q000737:chemistry* / Q000528:radiation effects; D013237:Stereoisomerism; D013941:Thymine / Q000031:analogs & derivatives* / Q000737:chemistry; D014466:Ultraviolet Rays; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
C520183:4-N-acetyl-2'-deoxycytidine; D003503:Cyclobutanes; D011740:Pyrimidine Dimers; D003841:Deoxycytidine; D014498:Uracil; D003596:Cytosine; D013941:Thymine