title: Synthesis and properties of oligonucleotides having a chemically stable 2-(trimethylsilyl)benzoyl group.
abstract: Acyl groups such as benzoyl and phenoxyacetyl have been used as a fundamental tool for protection of reactive hydroxyl and amino groups in chemical synthesis of DNA and RNA oligomers. It is well known that such protecting groups can be easily cleaved under basic conditions. Here we report 2-(trimethylsilyl)benzoyl (TMSBz), i.e., a chemically stabilized benzoyl group that is substituted with a trimethylsilyl group at its 2-position. To the best of our knowledge, the TMSBz group is the most resistant to basic conditions as an acyl group in nucleic acid chemistry.
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259 Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
authors.forename: Ken
authors.initials: K
authors.lastname: Yamada
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Taguchi
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013936:Thymidine / Q000031:analogs & derivatives*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives*
chemical_list: C541624:2-(trimethylsilyl)benzoic acid; D001565:Benzoates; D009838:Oligodeoxyribonucleotides; D014297:Trimethylsilyl Compounds; D013936:Thymidine; D014529:Uridine