title: Synthesis of acetylene-substituted probes with benzene-phosphate backbones for RNA labeling.
abstract: Conversion of dimethyl 5-aminoisophthalate into the iodoarene via the corresponding diazonium intermediate, followed by Sonogashira coupling with trimethylsilylacetylene afford the alkynylarene, which is reduced with LiAlH4 to give 5-ethynyl-1,3-benzenedimethanol (B(E)). One hydroxyl group is protected with a 4,4'-dimethoxytrityl (DMTr) group and subsequently another hydroxyl group is phosphitylated to produce the phosphoramidite. The mono-DMTr compound is also modified to afford the corresponding succinate, which is then reacted with controlled pore glass (CPG) to provide the solid support. Either the phosphoramidite or the solid support is employed in solid-phase synthesis of RNA containing B(E). RNA oligomers bearing B(E) rapidly react with 4-fluorobenzylazide to produce the cycloaddition products in good to excellent yield.
authors: Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu, Japan.
authors: Yoshiaki
authors: Y
authors: Kitamura
authors: Yoshihito
authors: Y
authors: Ueno
authors: Yukio
authors: Y
authors: Kitade
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D017607:Aluminum Compounds / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry*; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D017607:Aluminum Compounds; D018020:Lithium Compounds; D015335:Molecular Probes; D009843:Oligoribonucleotides; C042073:lithium aluminum hydride; D001554:Benzene; D000114:Acetylene
keywords: Huisgen cycloaddition; RNA labeling; alkynes; click chemistry