title: 5-Nitroindole as an universal base analogue.
abstract: 4-, 5- and 6-Nitroindole have been investigated and compared with 3-nitropyrrole as universal bases in oligodeoxynucleotides. Of these the 5-nitroindole derivative was found to be superior giving higher duplex stability, and behaving indiscriminately towards each of the four natural bases in duplex melting experiments. 3-Nitropyrrole, whilst not discriminating between the natural bases, was found to lead to considerable destabilisation of the duplexes, particularly when multiple substitutions were made, in contrast to the 5-nitroindole nucleoside.
authors.affiliation: Medical Research Council, Laboratory of Molecular Biology, Cambridge, UK.
authors.forename: D
authors.initials: D
authors.lastname: Loakes
authors.forename: D M
authors.initials: DM
authors.lastname: Brown
mesh_terms: D001483:Base Sequence; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004355:Drug Stability; D006358:Hot Temperature; D007211:Indoles / Q000737:chemistry*; D008969:Molecular Sequence Data; D009705:Nucleosides / Q000138:chemical synthesis*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D007211:Indoles; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; C090067:5-nitroindole