1245703-92-7Relevant academic research and scientific papers
Solid-supported synthesis and click conjugation of 4′- C -alkyne functionalized oligodeoxyribonucleotides
Kiviniemi, Anu,Virta, Pasi,L?nnberg, Harri
, p. 1890 - 1901 (2011/11/12)
4′-C-[N,N-Di(4-pentyn-1-yl)aminomethyl]thymidine and 4′-C-[N-methyl-N-(4-pentyn-1-yl)aminomethyl]thymidine 3′-(2- cyanoethyl-N,N-diisopropyl)phosphoramidites (1, 2) were synthesized, and one or two such monomers were incorporated into a 15-mer oligodeoxyribonucleotide. After chain assembly, azido-functionalized ligands, including appropriate derivatives of 1,4-phenylenedimethaneamine, mannose, paromamine, and neomycin, were conjugated to the alkynyl groups by the click chemistry on a solid support. The influence of the 4′-modifications on the melting temperature with DNA and 2′-O-methyl RNA targets was studied. Oligonucleotides containing one to four mannose ligands in the central part of the chain (up to two 4′-C-[N,N-di(4-pentyn-1-yl)aminomethyl]thymidine units) form equally stable duplexes with complementary 2′-OMe RNA as the corresponding unmodified DNA sequence. At high salt content, the mannose conjugation is even stabilizing. On using a DNA target, a modest destabilization occurs. All the amino group bearing conjugates stabilized the duplexes, the DNA?DNA duplexes more than the DNA?2′-O-methyl RNA duplexes.
