Orthoester protecting groups

Details Orthoester protecting groups Orthoester protecting groups

1998-02-27

2000-08-29

Wilson, James O.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 231, 536 2533, 536 2534, 536 2626, 536 267, 536 2671, 536 2672, 536 2673, 536 2674, C07H 1700

Patent

active

061110868

ABSTRACT:
Novel orthoesters are provided which can be used as a 2'-hydroxyl protecting groups or 2'-modification in the synthesis of polymers containing ribonucleic acid (RNA) nucleotides. The RNA comprising the orthoester can be handled and analyzed while 2'-modified, thereby minimizing potential degradation. The orthoester is stable during oligonucleotide synthesis. The orthoester is subsequently modified and can then be removed under mild acidic conditions. The ease and dependability of this process and the quality of the RNA product synthesized with this invention are comparable to that previously associated only with DNA synthesis.

REFERENCES:
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 4458066 (1984-07-01), Caruthers et al.
Rastogi, H., et al., "A new 2'-hydroxyl protecting group for the automated synthesis of oligoribonucleotides," Nucleic Acids Res., 23, pp. 4872-4877 (1995).
Capaldi, et al., "Use of the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and related protecting groups in oligoribonucleotide synthesis: stability of internucleotide linkages to aqueous acid," Nucleic Acids Res., 22, pp. 2209-2216 (1994).
Rao, M.V., et al, "Use of the 1-(2-Fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) protecting group in the solid-phase synthesis of oligo- and poly-ribonucleotides," J. Chem. Soc. Perkins Trans., 2, pp. 43-55 (1993).
Hata, T., et al, "2-chloroethyl orthoformate as a reagent for protection in nucleotides synthesis," Tetrahedron Lett., 51, pp. 4443-4446 (1969).
Sakatsume, O., et al, "Synthesis and properties of non-hammerhead RNA using 1-(2-chloroethoxy)-ethyl group for the protection of 2'-hydroxyl function," Nucleosides & Nucleotides, 10, pp. 141-153 (1991).
Sekine, M. et al, "Cyclic orthoester functions as new protecting groups in nucleosides," J. Am. Chem. Soc., 105, 2044-2049 (1983).
Beaucage, S.L., et al, "Advances in the synthesis of oligonucleotides by the phosphoramidite approach," Tetrahedron, 48, pp. 2223-2311 (1992).

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