Stereoselective formation of a cyclobutane pyrimidine dimer by using N4-acetyl protection of the cytosine base | Zendy

Katsuhisa Nishiguchi | Zendy; Junpei Yamamoto | Zendy; Shigenori Iwai | Zendy

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Stereoselective formation of a cyclobutane pyrimidine dimer by using N4-acetyl protection of the cytosine base

Author(s) -

Katsuhisa Nishiguchi,

Junpei Yamamoto,

Shigenori Iwai

Publication year - 2008

Publication title -

nucleic acids symposium series

Language(s) - English

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/nrn222

Subject(s) - cyclobutane , chemistry , pyrimidine dimer , cytosine , pyrimidine , deamination , uracil , thymine , dimer , glycosidic bond , stereochemistry , dna , photochemistry , biochemistry , dna damage , organic chemistry , ring (chemistry) , enzyme

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.

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