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Nucleoside Macrocycles Formed By Intramolecular Click Reaction: Efficient Cyclization Of Pyrimidine Nucleosides Decorated With 5'-azido Residues And 5-octadiynyl Side Chains

Jiang Liu, Peter Leonard, Sebastian L Müller, Constantin Daniliuc, Frank Seela

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Copper(I)-promoted "click" cyclization in the presence of TBTA afforded nucleoside macrocycles in very high yields (≈70%) without using protecting groups. To this end, dU and dC derivatives functionalized at the 5-position of the nucleobase with octadiynyl side chains and with azido groups at the 5’-position of the sugar moieties were synthesized. The macrocycles display freely accessible Watson–Crick recognition sites. The conformation of the 16-membered macrocycle was deduced from X-ray analysis and 1H,1H-NMR coupling constants. The sugar conformation (N vs S) was different in solution as compared to the solid state.