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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geprüft am 01.06.2024