Synthesis and properties of 5,6-dichlorobenzimidazole 2'----5'- and 3'----5'-nucleotide dimers and trimers.
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole (2), synthesised by the fusion method, was used for the synthesis of 2'----5'- and 3'----5'-linked di- and tri-meric oligonucleotides. The protecting groups used were p-methoxytrityl for HO-5', tert-butyldimethylsilyl for HO-2',3', and 2,5-dichlorophenyl and 2-(4-nitrophenyl)ethyl for the phosphate group. The internucleotidic linkages were established by the phosphotriester approach to give the fully protected 2'----5' dimers (15, 17, and 18) and trimers (27 and 28), as well as the 3'----5' dimers (22 and 23) and trimers (31 and 32). Deprotection involved a sequence of steps to afford the corresponding free oligonucleotides 21, 26, 30, and 33 isolated as the triethylammonium salts in good yields. The new compounds were characterised by elemental analysis and by u.v. and 1H-n.m.r. spectroscopy.
Ruf
K
K
Fakultät für Chemie Universität Konstanz, F.R.G.
Pfleiderer
W
W
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D004004:Dichlororibofuranosylbenzimidazole; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry
D000998:Antiviral Agents; D009841:Oligonucleotides; D004004:Dichlororibofuranosylbenzimidazole