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“Photoclick” Postsynthetic Modification of DNA
Author(s) -
Arndt Stefanie,
Wagenknecht HansAchim
Publication year - 2014
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.201407874
Subject(s) - maleimide , cycloaddition , chemistry , oligonucleotide , bioorthogonal chemistry , combinatorial chemistry , copper , dna , polymer chemistry , organic chemistry , catalysis , click chemistry , biochemistry
A new DNA building block bearing a push–pull‐substituted diaryltetrazole linked to the 5‐position of 2′‐deoxyuridine through an aminopropynyl group was synthesized. The accordingly modified oligonucleotide allows postsynthetic labeling with a maleimide‐modified sulfo‐Cy3 dye, N‐methylmaleimide, and methylmethacrylate as dipolarophiles by irradiation at 365 nm (LED). The determined rate constant of (23±7) M −1 s −1 is remarkably high with respect to other copper‐free bioorthogonal reactions and comparable with the copper‐catalyzed cycloaddition between azides and acetylenes.