Synthesis and NMR characterization of a novel crown-ether ring-fused uridine analogue |
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| Authors: | Cinzia Coppola Roberta Trotta Antonio Randazzo |
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| Institution: | a Dipartimento di Chimica Organica e Biochimica, Complesso Universitario di Monte S. Angelo, via Cintia, 4, Università degli Studi di Napoli ‘Federico II’, I-80126 Napoli, Italy
b Dipartimento di Chimica delle Sostanze Naturali, via D. Montesano 48, Università degli Studi di Napoli ‘Federico II’, I-80131 Napoli, Italy |
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| Abstract: | The chemical synthesis and 1H NMR analysis of a novel bicyclic uridine derivative, with a 18-crown-6 ether moiety fused at the ribose 2- and 3-positions, as first example of a hitherto unknown class of ribose-modified nucleosides, are here described. NMR-based conformational analysis studies showed for the modified nucleoside a marked preference for an N-type sugar puckering and the nucleobase in the anti conformation, with the uracil favouring the coordination of a sodium ion hosted in the crown ether. |
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| Keywords: | Nucleosides Crown ether derivatives Cyclization Protecting groups NMR analysis |
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