IMIDAZOLE TETHERED OLIGODEOXYRIBONUCLEOTIDES - SYNTHESIS AND RNA CLEAVING ACTIVITY



: HOVINEN J, GUZAEV A, AZHAYEVA E, AZHAYEV A, LONNBERG H

Publisher: AMER CHEMICAL SOC

: 1995

Journal of Organic Chemistry

JOURNAL OF ORGANIC CHEMISTRY

: J ORG CHEM

: 60

: 7

: 2205

: 2209

: 5

: 0022-3263

DOI: https://doi.org/10.1021/jo00112a047


A solid support (3) and a non-nucleosidic phosphoramidite building block (4), both containing a thioester bond is their structure, were synthesized. They were used in the preparation of oligonucleotides tethered 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 oligonucleotide by using the primary amino group of histamine or 1-(3-aminopropyl)imidazole as a nucleophile. The ability of the tethered oligonucleotides to hydrolyze complementary RNA strands was tested. Of the oligonucleotides prepared, 12b, bearing a histamine group at the 3'-end, was shown to promote a sequence specific strand scission of RNA in the presence of Zn2+ ions.



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