title: Synthesis of DNA conjugates with metalated tetracationic porphyrins by postsynthetic cycloadditions.
abstract: Tetracationic porphyrins of the TMPP (meso-tetra-(4-N-methylpyridyl)porphyrin) type, metalated with Cu(II) or with Au(III), were conjugated covalently to oligonucleotides. The Cu(I)-catalyzed cycloaddition (between an azide and an ethynyl group) and the Diels-Alder cycloaddition (between a furan and a maleimide functionality) were successfully applied as two alternative postsynthetic methods to modify the 2'-position of an internal uridine. Melting temperatures and UV/vis absorption properties were compared. CD measurements indicated that the type of conjugation chemistry determines the grade of intercalation of the attached and positively charged porphyrins.
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry , Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Wellner
authors.forename: Hans-Achim
authors.initials: HA
authors.lastname: Wagenknecht
mesh_terms: D002942:Circular Dichroism; D061565:Cycloaddition Reaction; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D007364:Intercalating Agents; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry*
chemical_list: D007364:Intercalating Agents; D009841:Oligonucleotides; D011166:Porphyrins; D004247:DNA