title: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012, Bern, Switzerland.
authors.forename: Stella
authors.initials: S
authors.lastname: Diafa
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012, Bern, Switzerland.
authors.forename: Damien
authors.initials: D
authors.lastname: Evéquoz
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012, Bern, Switzerland.
authors.forename: Christian J
authors.initials: CJ
authors.lastname: Leumann
authors.affiliation: Department of Structural Biology and Chemistry, Institut Pasteur, CNRS UMR3523, 28, rue du Docteur Roux, 75724, Paris Cedex 15, France.
authors.forename: Marcel
authors.identifier: http://orcid.org/0000-0003-0263-9206
authors.initials: M
authors.lastname: Hollenstein
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000378:metabolism*; D004247:DNA / Q000096:biosynthesis* / Q000737:chemistry; D004259:DNA-Directed DNA Polymerase / Q000737:chemistry / Q000378:metabolism*; D008968:Molecular Conformation; D009841:Oligonucleotides / Q000096:biosynthesis* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D009841:Oligonucleotides; D004247:DNA; D004259:DNA-Directed DNA Polymerase
keywords: DNA polymerases; bicyclo-DNA; modified nucleic acids; nucleoside triphosphates; oligonucleotides