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Novel base-labile protecting groups for 5'-hydroxyl protection in the synthesis of oligonucleotides. 2002

Kazuo Kamaike, and Takashi Namiki, and Yoshihiro Kayama, and Etsuko Kawashima
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

The 6-(levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl (LMM0NBz) and 2-(levulinyloxy-methyl)-5-methoxy-4-nitrobenzoyl (LMMpNBz) groups were developed as novel base-labile protection for the 5'-hydroxyl group in solid-phase oligonucleotide synthesis. A comparative study on the utility of LMMoNBz, LMMpNBz, and 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) groups for the synthesis of oligodeoxyribonucleotides, and the synthesis of oligoribonucleotides using the LMMoNBz group in combination with the acid-labile 1-ethoxyethylk (EE) group to protect the 2'-hydroxyl group, are described.

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
D017665 Hydroxyl Radical The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.

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