Nucleosides and nucleotides. 121. Synthesis of oligonucleotides carrying linker groups at the 1'-position of sugar residues.
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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Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Dan
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Matsuda
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D050260:Carbohydrate Metabolism; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003432:Cross-Linking Reagents / Q000737:chemistry*; D004355:Drug Stability; D004720:Endonucleases / Q000378:metabolism; D015870:Gene Expression / Q000187:drug effects; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D009711:Nucleotides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000378:metabolism; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis / Q000494:pharmacology; D016914:Ribonuclease H / Q000378:metabolism
D002241:Carbohydrates; D003432:Cross-Linking Reagents; D009705:Nucleosides; D009711:Nucleotides; D009841:Oligonucleotides; D016376:Oligonucleotides, Antisense; D004720:Endonucleases; D016914:Ribonuclease H