The synthesis and properties of oligoribonucleotide-spermine conjugates.
Polyamines stabilise nucleic acids against chemical and enzymatic degradation, facilitate the formation of secondary and tertiary structures and enhance cellular uptake. Therefore methods for the syntheses of polyamine-nucleic acid conjugates are of interest. A route for the syntheses of RNA-spermine conjugates has been developed. The polyamine was introduced to the C-5 position of uridine via an ethyl tether and the molecule elaborated into a synthon suitable for oligoribonucleotide assembly. The resultant oligomers were components of the hairpin ribozyme. Characterisation of the spermine-conjugated catalytic RNA revealed that attachment of the polyamine was well tolerated in three of four positions, namely U41, U37 and U34, suggesting that conjugation to C-5 brings about minimal structural perturbation.
Marsh
Andrew J
AJ
Centre for Chemical Biology, Department of Chemistry, Krebs Institute, University of Sheffield, Brook Hill, Sheffield, UKS3 7HF.
Williams
David M
DM
Grasby
Jane A
JA
D001483:Base Sequence; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D011073:Polyamines / Q000737:chemistry; D012313:RNA / Q000138:chemical synthesis; D016337:RNA, Catalytic / Q000138:chemical synthesis / Q000737:chemistry; D013096:Spermine / Q000138:chemical synthesis* / Q000737:chemistry*; D014529:Uridine / Q000138:chemical synthesis / Q000737:chemistry
D009843:Oligoribonucleotides; D011073:Polyamines; D016337:RNA, Catalytic; C418481:hairpin ribozyme; D013096:Spermine; D012313:RNA; D014529:Uridine