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| - Preparation of Azacrown-Functionalized 2‘-O-MethylOligoribonucleotides, Potential Artificial RNases
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| - An improved synthesis for 3-(3-aminopropyl)- and 3-(3-mercaptopropyl)-1,5,9-triazacyclododecane hasbeen developed and alternative methods for their conjugation to oligonucleotides have been described.Accordingly, the 3-aminopropyl azacrown and its N-(3-aminopropanoyl)-3-aminopropyl analogue havebeen tethered to the 3‘-terminus of a 2‘-O-methyloligoribonucleotide by aminolytic cleavage of thethioester linker utilized for the chain assembly. Studies on a monomeric model compound verify thatthe reaction proceeds solely by the attack of the primary amino group. 5‘-Conjugation has been achievedby introducing a 2-benzylthio-2-oxoethyl group to the 5‘-terminus as a phosphoramidite reagent andcleaving the thioester bond with the 3-aminopropyl azacrown. For intrachain conjugation, aphosphoramidite reagent derived from 1-deoxy-1-(2-benzylthio-2-oxoethyl)-β-d-erythro-pentofuranosehas been inserted in a desired position within the chain and subjected to on-support aminolysis withthe 3-aminopropyl azacrown or its N-(3-aminopropanoyl)-3-aminopropyl and N-(6-aminohexanoyl)-3-aminopropyl analogues. The 3-mercaptopropyl-derivatized azacrown has been tetherd by a disulfidebond to a 3‘-(3-mercaptoalkyl)phosphate-tailed oligonucleotide. The 3‘- and intrachain-tetheredconjugates have been shown to cleave as their Zn(II) chelate complementary oligoribonucleotidesequences.
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