{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Frei S"],"funding":["Swiss National Science Foundation"],"pagination":["3088-3097"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC6317435"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["14"],"pubmed_abstract":["Here we report on the synthesis, biophysical properties and molecular modeling of oligonucleotides containing unsaturated 6'-fluoro[4.3.0]bicyclo nucleotides (6'F-bc<sup>4,3</sup>-DNA). Two 6'F-bc<sup>4,3</sup> phosphoramidite building blocks (T and C) were synthesized starting from a previously described [3.3.0]bicyclic sugar. The conversion of this sugar to a <i>gem</i>-difluorinated tricyclic intermediate via difluorocarbene addition followed either by a NIS-mediated or Vorbrüggen nucleosidation yielded in both cases the β-tricyclic nucleoside as major anomer. Subsequent desilylation and cyclopropane ring opening of these tricyclic intermediates afforded the unsaturated 6'F-bc<sup>4,3</sup> nucleosides. The successful incorporation of the corresponding phosphoramidite building blocks in"],"journal":["Beilstein journal of organic chemistry"],"pubmed_title":["6'-Fluoro[4.3.0]bicyclo nucleic acid: synthesis, biophysical properties and molecular dynamics simulations."],"pmcid":["PMC6317435"],"funding_grant_id":["200020","165778"],"pubmed_authors":["Leumann CJ","Istrate A","Frei S"],"additional_accession":[]},"is_claimable":false,"name":"6'-Fluoro[4.3.0]bicyclo nucleic acid: synthesis, biophysical properties and molecular dynamics simulations.","description":"Here we report on the synthesis, biophysical properties and molecular modeling of oligonucleotides containing unsaturated 6'-fluoro[4.3.0]bicyclo nucleotides (6'F-bc<sup>4,3</sup>-DNA). Two 6'F-bc<sup>4,3</sup> phosphoramidite building blocks (T and C) were synthesized starting from a previously described [3.3.0]bicyclic sugar. The conversion of this sugar to a <i>gem</i>-difluorinated tricyclic intermediate via difluorocarbene addition followed either by a NIS-mediated or Vorbrüggen nucleosidation yielded in both cases the β-tricyclic nucleoside as major anomer. Subsequent desilylation and cyclopropane ring opening of these tricyclic intermediates afforded the unsaturated 6'F-bc<sup>4,3</sup> nucleosides. The successful incorporation of the corresponding phosphoramidite building blocks in","dates":{"release":"2018-01-01T00:00:00Z","publication":"2018","modification":"2026-05-07T02:51:30.815Z","creation":"2019-03-26T22:36:52Z"},"accession":"S-EPMC6317435","cross_references":{"pubmed":["30643586"],"doi":["10.3762/bjoc.14.288"]}}