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Synthesis of DNA Interstrand Cross‐Links Using a Photocaged Nucleobase
Author(s) -
Hentschel Sarah,
Alzeer Jawad,
Angelov Todor,
Schärer Orlando D.,
Luedtke Nathan W.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201108018
Subject(s) - moiety , dna , nucleobase , chemistry , deoxyguanosine , computer science , combinatorial chemistry , stereochemistry , computational biology , biochemistry , biology
The missing linking : BCNU is a chemotherapy drug that generates an ethylene bridge between N 1 of deoxyguanosine and N 3 of deoxycytidine. No synthesis of a DNA containing this moiety has been reported until now. A new strategy uses a photocaged nucleobase that, when released, generates a highly reactive intermediate which cross‐links the opposing DNA strand in a manner analogous to BCNU (see scheme, NBOC= ortho ‐nitrobenzyloxycarbonyl).