J. Hovinen et al., IMIDAZOLE TETHERED OLIGODEOXYRIBONUCLEOTIDES - SYNTHESIS AND RNA CLEAVING ACTIVITY, Journal of organic chemistry, 60(7), 1995, pp. 2205-2209
A solid support (3) and a non-nucleosidic phosphoramidite building blo
ck (4), both containing a thioester bond is their structure, were synt
hesized. They were used in the preparation of oligonucleotides tethere
d to an imidazole group at their 3'- or 5'-terminus, as well as at the
1'-position of nonterminal 3'-deoxypsicothymidine units. The desired
functional groups were introduced during the deprotection of the oligo
nucleotide by using the primary amino group of histamine or 1-(3-amino
propyl)imidazole as a nucleophile. The ability of the tethered oligonu
cleotides to hydrolyze complementary RNA strands was tested. Of the ol
igonucleotides prepared, 12b, bearing a histamine group at the 3'-end,
was shown to promote a sequence specific strand scission of RNA in th
e presence of Zn2+ ions.