Conformationally locked nucleosides. Synthesis of oligodeoxynucleotides containing 3'-amino-3'-deoxy-3'-N,5'(R)-C-ethylenethymidine.
3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5'(R)-C-ethylenethymidine (6) was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.
Wang
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Chemistry Laboratory, ICN Pharmaceuticals, Inc, Costa Mesa, California 92626, USA.
Stoisavljevic
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D004247:DNA / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D013696:Temperature; D013936:Thymidine / Q000031:analogs & derivatives / Q000032:analysis*
C420271:3'-amino-3'-deoxy-3'-N,5'-C-ethylenethymidine; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D012313:RNA; D004247:DNA; D013936:Thymidine