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Diplomarbeit aus dem Jahr 1993 im Fachbereich Chemie Organische Chemie, Note: 1,5, Universitt Osnabrck, Sprache: Deutsch, Abstract: 1) 2'Desoxyisoguanosin (1) wurde in einer zweistufigen Synthese dargestellt. Zu diesem Zweck wurde 2'Desoxyguanosin (3) zunchst in 2Amino2'desoxyadenosin (5) berfhrt. Dieses wurde in 2'Desoxyisoguanosin (1) umgewandelt. Bei der Reaktion von 2'Desoxyisoguanosin (1) mit Chloracetaldehyd bildete sich N6Etheno2'desoxyisoguanosin (9). Dieses zeigte mit N6Ethenoadenosin (6) vergleichbare Fluoreszenzeigenschaften. 2) 2',3'Didesoxyisoguanosin (2) konnte ber den photochemischen Austausch des 2Substituenten von 2Chlor2',3'didesoxyadenosin (20) dargestellt werden. Verbindung 20 konnte ber zwei Synthesewege gewonnen werden: Anfnglich ausgehend von 2Chlor2'desoxyadenosin (16) ber BartonDesoxygenierung in 27 % Gesamtaubeute ber vier Stufen. Alternativ wurde in einem konvergenten Syntheseweg der 2',3'Didesoxyzucker 21 mit 2,6Dichlorpurin (23) unter MitsunobuBedingungen umgesetzt. Durch nachfolgenden Austausch des 6Substituenten gegen NH2 waren die anomeren 6Amino2chlor2',3'didesoxynucleoside (25a, 25b) zugnglich. 3) Mit Hilfe der Festphasensynthese wurde das Oligomer d(iGC)3 (32) synthetisiert und seine Zusammensetzung durch enzymatische Hydrolyse bewiesen. Anhand des TmWertes von 29 C konnte die iGddCBasenpaarung nachgewiesen werden. Da alternierende iGddC Sequenzen nur unter paralleler Strangorientierung selbstkomplementr sind, resultiert im Vergleich zu d(GC)3 (33) der Verlust eines Basenpaares. Der parallele Duplex von d(iGC)3 wies mit 29C einen geringeren TmWert als d(GC)3 (45C) auf. Mit Hilfe von Inkrementberechnungen fr die freie Enthalpie pro Basenpaar, konnte bewiesen werden, da diese Destabilisierung von d(iGC)3 (32) durch die Einbue eines Basenpaares ausgelst wurde.
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