Process of linking nucleosides with a siloxane bridge

Details Process of linking nucleosides with a siloxane bridge Process of linking nucleosides with a siloxane bridge

1990-09-12

1993-05-25

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 2531, 536 2533, 536 2534, C07H 19173, C07H 19073, C07H 2104

Patent

active

052141349

ABSTRACT:
A method of linking nucleosides with a siloxane bridge comprising reacting a 3'-silylated-5'-protected nucleoside with an unprotected nucleoside is disclosed. The silylated and unprotected nucleosides may be either monomeric nucleosides or the terminal nucleosides of an oligonucleotide or oligonucleotide analog. A method of synthesizing an oligonucleotide analog having siloxane internucleoside linkages is also disclosed. The method of synthesis comprises silylating a 5'-protected nucleoside with a bifunctional silylating reagent to form a 3'-silylated nucleoside, reacting the silylated nucleoside with an unprotected nucleoside in the presence of a base catalyst and repeating these steps to form an oligonucleotide analog. A modified solid phase synthesis method for preparing an oligonucleotide analog having siloxane internucleoside linkages is also disclosed.

REFERENCES:
patent: 4959463 (1990-09-01), Froehler et al.
Ogawa, Nippon Nogei Kagaku Kaisha, 52(7), R93-R101 (1978); see also Chem. Abstr., 89:215,672u (1978).
Vroom et al., Nucleic Acids Research, 16(7),2987-3003 (1988).
Ishii et al., J. Chromatography, 218, 189-197 (1981).
Kochetkov et al., Organic Chemistry of Nucleic Acids, Part B, Plenum Press, New York, 1972, pp. 460-461.
Schneider et al., "Building Blocks for Oligonucleotide Analogs with Dimethylene-Sulfide, -Sulfoxide, and -Sulfone Groups Replacing Phosphodiester Linkages", Tetrahedron Letters, vol. 31, No. 3, pp. 335-338, 1990.
Ogilvie et al., "Synthesis of a Thymidine Dinucleotide Analogue Containing an Internucleotide Silyl Linkage", Tetrahedron Letters, vol. 26, No. 35, pp. 4159-4162, 1985.
Cormier et al., "Synthesis of Hexanucleotide Analogues Containing Diisopropylsilyl Internucleotide Linkages", Nucleic Acids Research, vol. 16, No. 10, pp. 4583-4594, 1988.

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