Stepwise Click Functionalization of DNA through a Bifunctional Azide with a Chelating and a Nonchelating Azido Group

Autor(en): Ingale, Sachin A.
Seela, Frank
Stichwörter: 1,3-DIPOLAR CYCLOADDITIONS; ALKYNE CYCLOADDITION; Chemistry; Chemistry, Organic; CROSS-LINKED DNA; DUPLEX STABILITY; OLIGONUCLEOTIDES; ORGANIC AZIDES; SIDE-CHAINS; SOLID SUPPORT; TERMINAL ALKYNES
Erscheinungsdatum: 2013
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 78
Ausgabe: 7
Startseite: 3394
Seitenende: 3399
Zusammenfassung: 
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 carrying the nonchelating 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.
ISSN: 00223263
DOI: 10.1021/jo400059b

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