Stepwise Click Functionalization of DNA through a Bifunctional Azide with a Chelating and a Non-Chelating Azido Group. a Ingale, S. & Seela, F. The Journal of organic chemistry, February, 2013. doi abstract bibtex A stepwise chemoselective click reaction was performed on nucleosides and oligonucleotides containing 7-octadiynyl-7-deaza-2'-deoxyguanosine and 5-octadiynyl-2'-deoxycytidine with unsymmetrical 2,5-bis(azidomethyl)pyridine using copper(II)acetate. The reaction is selective for the chelating azido group thereby forming monofunctionalized adducts still carring the non-chelating azido functionality. The azido-functionalized adduct was applied to a second click reaction, now performed in the presence of reducing agent, to generate cross-linked DNA or a pyrene click conjugate. The chelate controlled stepwise click reaction is applicable to alkynylated nucleosides and oligonucleotides.
@article{Ingale2013,
title = {Stepwise Click Functionalization of {{DNA}} through a Bifunctional Azide with a Chelating and a Non-Chelating Azido Group.},
author = {a Ingale, Sachin and Seela, Frank},
year = {2013},
month = feb,
journal = {The Journal of organic chemistry},
eprint = {23437864},
eprinttype = {pubmed},
issn = {1520-6904},
doi = {10.1021/jo400059b},
abstract = {A stepwise chemoselective click reaction was performed on nucleosides and oligonucleotides containing 7-octadiynyl-7-deaza-2'-deoxyguanosine and 5-octadiynyl-2'-deoxycytidine with unsymmetrical 2,5-bis(azidomethyl)pyridine using copper(II)acetate. The reaction is selective for the chelating azido group thereby forming monofunctionalized adducts still carring the non-chelating azido functionality. The azido-functionalized adduct was applied to a second click reaction, now performed in the presence of reducing agent, to generate cross-linked DNA or a pyrene click conjugate. The chelate controlled stepwise click reaction is applicable to alkynylated nucleosides and oligonucleotides.},
pmid = {23437864},
keywords = {\#nosource}
}
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