Synthesis of 2-amino-2-deoxy-β-glycosyl-(1→5)-nucleosides and the interaction with RNA

Add time:09/09/2019    Source:sciencedirect.com

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranose and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-d-galactopyranose reacted with protected nucleosides in the presence of BF3 as promoter at room temperature to give selectively 2-amino-2-deoxy-β-glycosyl (1→5)nucleosides in good yields. CD spectra and thermal melting studies showed that 2-amino-2-deoxy-β-d-glucopyranosyl-(1→5)-nucleosides could interact with RNA in solution and 2-deoxy-2-amino-β-d-galactopyranosyl-(1→5)-nucleosides (17–19) exhibit higher affinity to RNA than 2-deoxy-2-amino-β-d-glucopyranosyl-(1→5)-nucleosides (14–16). It indicated that the majority of interactions are established between the polar group of glycosylnucleosides and the sugar-phosphate backbone of RNA helices and weak stacking interaction is observed. The different configuration of hydroxyl group on the glycosyl moiety may affect the glycosyl-nucleoside binding to RNA by induced fit.

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