title: Interstrand cross-link and bioconjugate formation in RNA from a modified nucleotide.
abstract: RNA oligonucleotides containing a phenyl selenide derivative of 5-methyluridine were chemically synthesized by solid-phase synthesis. The phenyl selenide is rapidly converted to an electrophilic, allylic phenyl seleneate under mild oxidative conditions. The phenyl seleneate yields interstrand cross-links when part of a duplex and is useful for synthesizing oligonucleotide conjugates. Formation of the latter is illustrated by reaction of an oligonucleotide containing the phenyl selenide with amino acids in the presence of mild oxidant. The products formed are analogous to those observed in tRNA that are believed to be formed posttranslationally via a biosynthetic intermediate that is chemically homologous to the phenyl seleneate.
authors.affiliation: Department of Chemistry, Johns Hopkins University , 3400 N. Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Jack L
authors.initials: JL
authors.lastname: Sloane
authors.forename: Marc M
authors.initials: MM
authors.lastname: Greenberg
mesh_terms: D003432:Cross-Linking Reagents / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012313:RNA / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D003432:Cross-Linking Reagents; D009711:Nucleotides; D009841:Oligonucleotides; D016566:Organoselenium Compounds; C009182:ribothymidine; D012313:RNA; D014529:Uridine