Synthesis and properties of oligonucleotides having a chemically stable 2-(trimethylsilyl)benzoyl group.
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.
Yamada
Ken
K
Department of Life Science, Tokyo Institute of Technology, 4259 Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Taguchi
Haruhiko
H
Ohkubo
Akihiro
A
Seio
Kohji
K
Sekine
Mitsuo
M
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*
C541624:2-(trimethylsilyl)benzoic acid; D001565:Benzoates; D009838:Oligodeoxyribonucleotides; D014297:Trimethylsilyl Compounds; D013936:Thymidine; D014529:Uridine