title: Synthesis of the first tellurium-derivatized oligonucleotides for structural and functional studies.
abstract: We report here the first synthesis of Te-nucleoside phosphoramidites and Te-modified oligonucleotides. We protected the 2'-tellurium functionality by alkylation and found that the Te functionality is compatible with solid-phase synthesis and that the Te oligonucleotides are stable during deprotection and purification. In addition, the redox properties of the Te functionalities have been explored. We found that the telluride and telluoxide DNAs are interchangeable by redox reactions. At elevated temperature, the Te-DNA can also be site-specifically fragmented oxidatively or reductively when 2'-TePh functionality is present, whereas elimination of the nucleobase is observed in the presence of 2'-TeMe. Moreover, the stability of the DNA duplexes derivatized with the Te functionalities has been investigated. Our Te derivatization of nucleic acids provides a novel approach for investigating DNA damage as well as for structure and function studies of nucleic acids and their protein complexes.
authors.affiliation: Department of Chemistry, Georgia State University, 50 Decatur Street, Atlanta, GA 30303-3083, USA.
authors.forename: Jia
authors.initials: J
authors.lastname: Sheng
authors.forename: Abdalla E A
authors.initials: AE
authors.lastname: Hassan
authors.forename: Zhen
authors.initials: Z
authors.lastname: Huang
mesh_terms: D002384:Catalysis; D003432:Cross-Linking Reagents; D018360:Crystallography, X-Ray; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D004249:DNA Damage; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013691:Tellurium / Q000737:chemistry*; D013696:Temperature
chemical_list: D003432:Cross-Linking Reagents; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D004247:DNA; D013691:Tellurium