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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