New strategies for oligonucleotide synthesis by use of 2-trimethylsilylethyl and 2-trimethylsilylethoxymethyl as the phosphate and 2'-hydroxyl protecting groups, respectively. 1993

T Wada, and M Tobe, and T Nagayama, and K Furusawa, and M Sekine
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.

The 2-Trimethylsilylethyl (TSE) group was found to be useful as a protecting group for the internucleotidic phosphate in DNA synthesis. Oligodeoxyribonucleotides were synthesized in good yields by using phosphoramidite building blocks having the TSE group. In RNA synthesis, 2-trimethylsilylethoxymethyl (SEM) group was introduced as a new protecting group for the 2'-hydroxyl. Selective protection of this function with SEM-Cl was achieved in good yield by use of 3',5'-O-bis(tert-butyl)silanediyl ribonucleoside derivatives.

UI MeSH Term Description Entries
D009841 Oligonucleotides Polymers made up of a few (2-20) nucleotides. In molecular genetics, they refer to a short sequence synthesized to match a region where a mutation is known to occur, and then used as a probe (OLIGONUCLEOTIDE PROBES). (Dorland, 28th ed) Oligonucleotide
D006900 Hydroxylation Placing of a hydroxyl group on a compound in a position where one did not exist before. (Stedman, 26th ed) Hydroxylations
D014297 Trimethylsilyl Compounds Organic silicon derivatives used to characterize hydroxysteroids, nucleosides, and related compounds. Trimethylsilyl esters of amino acids are used in peptide synthesis. Compounds, Trimethylsilyl

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