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© Research
Publication : Chembiochem : a European journal of chemical biology

Synthesis and biochemical characterization of tricyclothymidine triphosphate (tc-TTP)

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Chembiochem : a European journal of chemical biology - 17 Jul 2014

Hollenstein M, Leumann CJ

Link to Pubmed [PMID] – 25044722

Chembiochem 2014 Sep;15(13):1901-4

Tricyclo-DNA (tc-DNA) is a conformationally restricted oligonucleotide analogue that exhibits promising properties as a robust antisense agent. Here we report on the synthesis and biochemical characterization of tc-TTP, the triphosphate of a tc-DNA nucleoside containing the base thymine. Tc-TTP turned out to be a substrate for the Vent (exo(-) ) DNA polymerase, a polymerase that allows for multiple incorporations of tc-T nucleotides under primer extension reaction conditions. However, the substrate acceptance is rather low, as also observed for other sugar-modified analogues. Tc-TTP and tc-nucleotide-containing templates do not sustain enzymatic polymerization under physiological conditions; this indicates that tc-DNA-based antisense agents will not enter natural metabolic pathways that lead to long-term toxicity.