Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA.
[reaction: see text] We report the development of the Cu(I)-catalyzed Huisgen cycloaddition (click) reaction for the multiple postsynthetic labeling of alkyne-modified DNA. A series of alkyne-modified oligodeoxyribonucleotides (ODNs) of increasing alkyne density were prepared, and the click reaction using various azide labels was investigated. Complete high-density conversion was observed for ODNs containing up to six consecutive alkyne functions. Compatibility of the click conditions with long DNA strands was shown using a PCR product obtained with an alkyne-modified primer.
Gierlich
Johannes
J
Ludwig-Maximilians University Munich, 81377 Munich, Butenandtstr. 5-13, Haus F, Germany.
Burley
Glenn A
GA
Gramlich
Philipp M E
PM
Hammond
David M
DM
Carell
Thomas
T
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*
D000480:Alkynes; D001386:Azides; D009838:Oligodeoxyribonucleotides; D003300:Copper; D004247:DNA