Site specific labelling of sugar residues in oligoribonucleotides: reactions of aliphatic isocyanates with 2' amino groups

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Abstract
Considerable effort has been directed towards studying the structure and function of nucleic acids and several approaches rely on the attachment of reporter groups or reactive functional groups to nucleic acids. We report here the selective modification of 2′-amino groups in oligoribonucleotides, through their reaction with aliphatic isocyanates, to give the corresponding 2′-urea derivatives in >95% yield. Furthermore, such modification with (2-isocyanato)ethyl 2-pyridyl disulfide enables subsequent coupling to other thiols (such as those contained in peptides and proteins) or to thiol-reactive electrophiles. A modified decamer was not significantly destabilized by the 2′-urea group, compared with a 2′-amino group, as demonstrated by a mere 1.3°C drop in the melting temperature of the duplex.