期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 7, 页码 3394-3399出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo400059b
关键词
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资金
- ChemBiotech, Munster, Germany
- Grants-in-Aid for Scientific Research [23390026] Funding Source: KAKEN
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.
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