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Oligonucleotides with a 3′−3′ inversion of polarity, containing an acridine moiety attached to the nucleotide base flanking the 3′−3′ phosphodiester bond, have been synthesised, characterised and used to form alternate-strand triple helix complexes. These have been investigated by UV melting studies and CD experiments. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

A high-yield synthesis of [1-15N]-2′-deoxyinosine (5), [4-15N]-2′-deoxyAICAR (7), and [1-15N]-2′-deoxyguanosine (10) from 2′-deoxyinosine (1) using relatively low expensive 15NH3 as 15N source is described. The method exploits 2-C reactivity of 2′-deoxyinosine (1) to obtain its 15N-labelled counterpart, through [1-15N]-2′-deoxyinosine (5), and successively, [4-15N]-2′-deoxyAICAR (7). [1-15N]-2′-Deoxyguanosine (10) can be prepared as well, through an improved cyclization procedure. No protection of sugar hydroxyl groups is required at any stage.

Ribosylation and glucosylation of the base residues of inosine and uridine have been efficiently achieved using Mitsunobu reaction, leading to the N-1 and 6-O-glycosylinosine and N-3-glycosyluridine derivatives, all with β configuration at the glycosidic carbon. The unprecedented 5-amino-1-(β-D-ribofuranosyl)imidazole-4-[N-(β-D-glucopyranosyl)carboxamide] has also been synthesised.

A new analogue of cyclic inosine diphosphate ribose (cIDPR), in which the N-1 and N-9 ribosyl moieties were substituted by an alkyl moiety and an hydroxy-alkyl chain, has been synthesized and characterized.