Sensitized photochemistry of di(4-tetrazolouracil) dinucleoside monophosphate as a route to dicytosine cyclobutane photoproduct precursors

The DNA cis-syn cyclobutane photoproduct formed between two adjacent cytosine residues is highly mutagenic and responsible for the tandem CC to TT transition. However, its instability has prevented its in vitro study, so far. With a view to prepare oligodeoxynucleotides containing the CC cyclobutane...

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Bibliographic Details
Published in:Photochemical & photobiological sciences 2013-08, Vol.12 (8), p.1366-1374
Main Authors: Peyrane, Frédéric, Clivio, Pascale
Format: Article
Language:English
Subjects:
Acetone - chemistry
Biochemistry
Biomaterials
Chemistry
Cytosine - analogs & derivatives
Dinucleoside Phosphates - chemistry
Physical Chemistry
Plant Sciences
Pyrimidine Dimers - chemistry
Ultraviolet Rays
Uracil - analogs & derivatives
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Summary:The DNA cis-syn cyclobutane photoproduct formed between two adjacent cytosine residues is highly mutagenic and responsible for the tandem CC to TT transition. However, its instability has prevented its in vitro study, so far. With a view to prepare oligodeoxynucleotides containing the CC cyclobutane lesion, we have synthesized in good yield a ditetrazolouracil cyclobutane dinucleotide photoproduct as a stable precursor of this photoproduct. Our approach also overcomes the low photochemical reactivity of the cytosine-cytosine deoxydinucleoside monophosphate.
ISSN:1474-905X
1474-9092
DOI:10.1039/c3pp25402j