Synthesis and Structural Characterization of 2′-Deoxy-2′-fluoro-<scp>l</scp>-uridine Nucleic Acids
Yuliya Dantsu, Ying Zhang, Wen Zhang
Abstract
Despite the development of artificial l-RNA/DNA as therapeutic molecules, the in-depth investigation on their chemical modifications is still limited. Here, we synthesize a chemically derivatized 2'-deoxy-2'-fluoro-l-uridine building block and incorporate it into oligonucleotides. Our thermo-denaturization and enzymatic digestion experiments reveal their superior stability. Furthermore, one crystal structure of l-type fluoro-DNA is determined to characterize its handedness. Our results reveal the increase of l-helix stability by fluoro-modification and provide the foundation for its future functional application.
Topics & Concepts
ChemistryOligonucleotideNucleic acidUridineDNARNACharacterization (materials science)Combinatorial chemistryHelix (gastropod)MoleculeSmall moleculeBiochemistryStereochemistryNanotechnologyOrganic chemistryGeneEcologySnailMaterials scienceBiologyDNA and Nucleic Acid ChemistryRNA modifications and cancerAdvanced biosensing and bioanalysis techniques