Invading Escherichia coli Genetics with a Xenobiotic Nucleic Acid Carrying an Acyclic Phosphonate Backbone (ZNA)
| Autor: | Piet Herdewijn, Elisabetta Groaz, Guy Schepers, Faten Jaziri, Min Luo, Mathy Froeyen, Philippe Marliere, Jef Rozenski, Valérie Pezo, Piotr Leonczak |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Circular dichroism
Stereochemistry THYMIDINE Chemistry Multidisciplinary Oligonucleotides Organophosphonates Gene Expression 010402 general chemistry medicine.disease_cause 01 natural sciences Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Models Nucleic Acids medicine Escherichia coli Nucleotide TRANSCRIPTION chemistry.chemical_classification Science & Technology biology CLICK-LINKED DNA Molecular Nucleic Acid Hybridization Models Molecular Nucleic Acid Conformation General Chemistry NUCLEOSIDE PHOSPHONATES IN-VITRO SEMISYNTHETIC ORGANISM Phosphonate EVOLUTION 0104 chemical sciences REPLACEMENT Chemistry Monomer chemistry Physical Sciences REPLICATION biology.protein Nucleic acid DUPLEX STRUCTURE DNA polymerase I DNA |
| Popis: | A synthetic orthogonal polymer embracing a chiral acyclic-phosphonate backbone [(S)-ZNA] is presented that uniquely adds to the emerging family of xenobiotic nucleic acids (XNAs). (S)-ZNA consists of reiterating six-atom structural units and can be accessed in few synthetic steps from readily available phophonomethylglycerol nucleoside (PMGN) precursors. Comparative thermal stability experiments conducted on homo- and heteroduplexes made of (S)-ZNA are described that evince its high self-hybridization efficiency in contrast to poor binding of natural complements. Although preliminary and not conclusive, circular dichroism data and dynamic modeling computations provide support to a left-handed geometry of double-stranded (S)-ZNA. Nonetheless, PMGN diphosphate monomers were recognized as substrates by Escherichia coli (E. coli) polymerase I as well as being imported into E. coli cells equipped with an algal nucleotide transporter. A further investigation into the in vivo propagation of (S)-ZNA culminated with the demonstration of the first synthetic nucleic acid with an acyclic backbone that can be transliterated to DNA by the E. coli cellular machinery. ispartof: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY vol:141 issue:27 pages:10844-10851 ispartof: location:United States status: published |
| Databáze: | OpenAIRE |
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