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New Light‐Sensitive Nucleosides for Caged DNA Strand Breaks
Author(s) -
Dussy Adrian,
Meyer Christoph,
Quennet Edith,
Bickle Thomas A.,
Giese Bernd,
Marx Andreas
Publication year - 2002
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/1439-7633(20020104)3:1<54::aid-cbic54>3.0.co;2-2
Subject(s) - thermus aquaticus , oligonucleotide , dna , chemistry , nucleoside , nucleotide , bond cleavage , cleavage (geology) , dna polymerase , combinatorial chemistry , polymerase , stereochemistry , photochemistry , biochemistry , biology , catalysis , paleontology , fracture (geology) , gene
Phototriggered bond cleavage has found wide application in chemistry as well as in biology. Nevertheless, there are only a few methods available for site‐specific photochemical induction of DNA strand scission despite numerous potential applications. In this study we report the development of new photocleavable nucleotides based on the photochemistry of o ‐nitrobenzyl esters. The light‐sensitive moieties were generated through introduction of o ‐nitrophenyl groups at the 5′ C position of the nucleoside sugar backbone. The newly synthesized, modified nucleosides were incorporated in oligonucleotides and are able to build stable DNA duplexes. In such a way modified oligonucleotides can be cleaved site‐specifically upon irradiation with >360 nm light with high efficiency. Furthermore, we show that these modifications can be bypassed in DNA synthesis promoted by Thermus aquaticus DNA polymerase.