Synthesis of Carbon-3-Substituted 1,5,9-Triazacyclododecanes, RNA Cleavage Agents Suitable for Oligonucleotide Tethering
- 1 January 1998
- journal article
- Published by American Chemical Society (ACS) in Bioconjugate Chemistry
- Vol. 9 (1), 132-136
- https://doi.org/10.1021/bc970108c
Abstract
Two derivatives of 1,5,9-triazacyclododecane bearing an alkylamino tether group at carbon-3 (7 and 13) were synthesized. The first of them, 7, was prepared starting from diethyl 2-(2-cyanoethyl)malonate and the second one, 13, from glycerol. In both cases, the cyclization reaction was performed by allowing the corresponding ditosylates (5 and 12) to react with TBD. The guanidinium salts formed were reduced in situ to the orthoamides (6 and 12), acid-catalyzed hydrolysis of which yielded the title compounds. The suitability of the azacrowns prepared for oligonucleotide tethering is also demonstrated.Keywords
This publication has 6 references indexed in Scilit:
- Imidazole Tethered Oligodeoxyribonucleotides: Synthesis and RNA Cleaving ActivityThe Journal of Organic Chemistry, 1995
- Selective Hydrolysis of tRNA by Ethylenediamine Bound to a DNA Oligomer1The Journal of Biochemistry, 1994
- Site-Specific Hydrolysis of RNA by Europium(III) Texaphyrin Conjugated to a Synthetic OligodeoxyribonucleotideJournal of the American Chemical Society, 1994
- Sequence-Specific Cleavage of HIV mRNA by a Ribozyme MimicJournal of the American Chemical Society, 1994
- Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: a powerful tool for the mass and sequence analysis of natural and modified oligonucleotidesNucleic Acids Research, 1993
- Biotinyl and phosphotyrosinyl phosphoramidite derivatives useful in the incorporation of multiple reporter groups on synthetic oligonucleotidesNucleic Acids Research, 1990