Synthesis of [15N]guanosines and deoxy[15N]guanosines from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (‘AICA-riboside’)

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Abstract
Methods are described for the syntheses of 15N-labelled guanosines and deoxyguanosines, suitable for incorporation into oligonucleotides. The 15N is located either at N-1 (e.g.[15N1]guanosine 1a and deoxy[15N1]guanosine 1b) or at the NH2(e.g.[15NH2]guanosine 1c and deoxy[15NH2]guanosine 1d). One of the synthetic methods starts from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (AICA-riboside, 2a) and leads via a cyclonucleoside to mixtures of compounds 1a and 1c, in which either compound predominates depending on the source of 15N (ammonia or benzoyl isothiocyanate). The other method utilises the same starting material, but a different mode of formation of the pyrimidine ring and yields either guanosine 1a or 1c(as its 2-N-benzoyl derivative 8b), exclusively.

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