title: Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA.
abstract: [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.
authors.affiliation: Ludwig-Maximilians University Munich, 81377 Munich, Butenandtstr. 5-13, Haus F, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Gierlich
authors.forename: Glenn A
authors.initials: GA
authors.lastname: Burley
authors.forename: Philipp M E
authors.initials: PM
authors.lastname: Gramlich
authors.forename: David M
authors.initials: DM
authors.lastname: Hammond
authors.forename: Thomas
authors.initials: T
authors.lastname: Carell
mesh_terms: 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*
chemical_list: D000480:Alkynes; D001386:Azides; D009838:Oligodeoxyribonucleotides; D003300:Copper; D004247:DNA