Synthesis of Oligonucleotides Containing 2′-Deoxyguanosine Adducts of Nitropyrenes

Two different approaches to synthesize oligonucleotides containing the 2 ′-deoxyguanosine adducts formed by nitropyrenes are described. A direct reaction of an unmodified oligonucleotide with an activated nitropyrene derivative is a convenient biomimetic approach for generating the major adducts in...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2009-02, Vol.28 (2), p.67-77
Main Authors: Colis, Laureen C., Chakraborti, Debasis, Hilario, Pablo, McCarty, Christopher, Basu, Ashis K.
Format: Article
Language:English
Subjects:
Deoxyguanosine - chemical synthesis
Deoxyguanosine - chemistry
dinitropyrene
DNA adducts
DNA Adducts - chemistry
Nitropyrene
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Pyrenes - chemistry
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Summary:Two different approaches to synthesize oligonucleotides containing the 2 ′-deoxyguanosine adducts formed by nitropyrenes are described. A direct reaction of an unmodified oligonucleotide with an activated nitropyrene derivative is a convenient biomimetic approach for generating the major adducts in DNA. A total synthetic approach, by contrast, involves several synthetic steps, including Buchwald-Hartwig Pd-catalyzed coupling, but can be used for incorporating both the major and minor adducts in DNA in high yield.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770902736426