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Enzymatic Synthesis of 7′,5′-Bicyclo-DNA Oligonucleotides

Abstract : The selection of artificial genetic polymers with tailor-made properties for their application in synthetic biology requires the exploration of new nucleosidic scaffolds that can be used in selection experiments. Herein, we describe the synthesis of a bicyclo-DNA triphosphate (i.e., 7',5'-bc-TTP) and show its potential to serve for the generation of new xenonucleic acids (XNAs) based on this scaffold. 7',5'-bc-TTP is a good substrate for Therminator DNA polymerase, and up to seven modified units can be incorporated into a growing DNA chain. In addition, this scaffold sustains XNA-dependent DNA synthesis and potentially also XNA-dependent XNA synthesis. However, DNA-dependent XNA synthesis on longer templates is hampered by competitive misincorporation of deoxyadenosine triphosphate (dATP) caused by the slow rate of incorporation of 7',5'-bc-TTP.
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Contributor : Marcel Hollenstein <>
Submitted on : Friday, February 8, 2019 - 3:53:41 PM
Last modification on : Monday, January 13, 2020 - 5:08:19 PM




Stella Diafa, Damien Evéquoz, Christian Leumann, Marcel Hollenstein. Enzymatic Synthesis of 7′,5′-Bicyclo-DNA Oligonucleotides. Chemistry - An Asian Journal, Wiley-VCH Verlag, 2017, 12 (12), pp.1347-1352. ⟨10.1002/asia.201700374⟩. ⟨pasteur-02012262⟩



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