title: Properties and reactivity of nucleic acids relevant to epigenomics, transcriptomics, and therapeutics.
abstract: Developments in epigenomics, toxicology, and therapeutic nucleic acids all rely on a precise understanding of nucleic acid properties and chemical reactivity. In this review we discuss the properties and chemical reactivity of each nucleobase and attempt to provide some general principles for nucleic acid targeting or engineering. For adenine-thymine and guanine-cytosine base pairs, we review recent quantum chemical estimates of their Watson-Crick interaction energy, π-π stacking energies, as well as the nuclear quantum effects on tautomerism. Reactions that target nucleobases have been crucial in the development of new sequencing technologies and we believe further developments in nucleic acid chemistry will be required to deconstruct the enormously complex transcriptome.
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, Basel, CH-4056, Switzerland. dennis.gillingham@unibas.ch.
authors.forename: Dennis
authors.initials: D
authors.lastname: Gillingham
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, Basel, CH-4056, Switzerland. dennis.gillingham@unibas.ch.
authors.forename: Stefanie
authors.initials: S
authors.lastname: Geigle
authors.affiliation: Department of Chemistry, University of Basel, Klingelbergstrasse 80, CH-4056 Basel, Switzerland.
authors.forename: O
authors.initials: O
authors.lastname: Anatole von Lilienfeld
mesh_terms: D000818:Animals; D004247:DNA / Q000737:chemistry / Q000235:genetics / Q000378:metabolism* / Q000627:therapeutic use*; D057890:Epigenomics / Q000379:methods*; D020869:Gene Expression Profiling / Q000379:methods*; D006801:Humans; D012313:RNA / Q000737:chemistry / Q000235:genetics / Q000378:metabolism* / Q000627:therapeutic use*
chemical_list: D012313:RNA; D004247:DNA