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Nucleosides and nucleotides. 121. Synthesis of oligonucleotides carrying linker groups at the 1'-position of sugar residues.

Bioconjugate chemistry (1993-11-01)
A Ono, A Dan, A Matsuda
RESUMEN

Novel 2'-deoxyuridine analogues carrying aminoalkyl linkers at the 1'-position of the sugar residues were synthesized and incorporated into oligonucleotides, then intercalating groups such as an anthraquinone derivative and a pyrene derivative were attached to the amino groups. Duplexes consisting of the oligonucleotides carrying the linker groups and a complementary ribonucleotide were more stable than an unmodified parent duplex, but the duplexes consisting of the oligonucleotides and a complementary deoxyribonucleotide were less stable. The oligonucleotides carrying the linker groups were more resistant to nuclease P1 and venom phosphodiesterase than an unmodified oligonucleotide. Furthermore, a duplex formed by the oligonucleotide analogue and the complementary ribonucleotide was a substrate for ribonuclease H.

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Sigma-Aldrich
2-Cyanoethyl N,N-diisopropylchlorophosphoramidite, Cl 13.5-15.5 %