title: Xylonucleic acid: synthesis, structure, and orthogonal pairing properties.
abstract: There is a common interest for studying xeno-nucleic acid systems in the fields of synthetic biology and the origin of life, in particular, those with an engineered backbone and possessing novel properties. Along this line, we have investigated xylonucleic acid (XyloNA) containing a potentially prebiotic xylose sugar (a 3'-epimer of ribose) in its backbone. Herein, we report for the first time the synthesis of four XyloNA nucleotide building blocks and the assembly of XyloNA oligonucleotides containing all the natural nucleobases. A detailed investigation of pairing and structural properties of XyloNAs in comparison to DNA/RNA has been performed by thermal UV-melting, CD, and solution state NMR spectroscopic studies. XyloNA has been shown to be an orthogonal self-pairing system which adopts a slightly right-handed extended helical geometry. Our study on one hand, provides understanding for superior structure-function (-pairing) properties of DNA/RNA over XyloNA for selection as an informational polymer in the prebiotic context, while on the other hand, finds potential of XyloNA as an orthogonal genetic system for application in synthetic biology.
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Mohitosh
authors.initials: M
authors.lastname: Maiti
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Munmun
authors.initials: M
authors.lastname: Maiti
authors.affiliation: Organic Materials Chemistry and Bioorganic Chemistry, Institute of Chemistry of New Materials, University of Osnabrück, Barbarastrasse. 7, D-49069 Osnabrück, Germany.
authors.forename: Christine
authors.initials: C
authors.lastname: Knies
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Shrinivas
authors.initials: S
authors.lastname: Dumbre
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Eveline
authors.initials: E
authors.lastname: Lescrinier
authors.affiliation: Organic Materials Chemistry and Bioorganic Chemistry, Institute of Chemistry of New Materials, University of Osnabrück, Barbarastrasse. 7, D-49069 Osnabrück, Germany.
authors.forename: Helmut
authors.initials: H
authors.lastname: Rosemeyer
authors.affiliation: Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
authors.forename: Arnout
authors.initials: A
authors.lastname: Ceulemans
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium Piet.Herdewijn@rega.kuleuven.be.
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D020029:Base Pairing; D004247:DNA / Q000737:chemistry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D009696:Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D012313:RNA / Q000737:chemistry; D014994:Xylose / Q000737:chemistry*
chemical_list: D009696:Nucleic Acids; D012313:RNA; D004247:DNA; D014994:Xylose