Process for synthesizing oligonucleotides and their analogs adap

Details Process for synthesizing oligonucleotides and their analogs adap Process for synthesizing oligonucleotides and their analogs adap

1989-04-06

1992-09-22

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 28, 536 29, C07H 2100

Patent

active

051497980

ABSTRACT:
A process of producing synthetic oligonucleotides on a small or large scale using H-phosphonate nucleoside monomers is described. The process can be used to synthesize oligonucleotides of any length, including oligodeoxyribonucleotides and oligoribonucleotides. The process results in a coupling efficiency of greater than 97% and consumes only two to three equivalents of monomer to activator per coupling reaction. In addition, the process does not require a separate capping step and capping reagent because the activating reagent serves a self-capping function thereby preventing elongation of failed sequences. The H-phosphonate linkages of the fully synthesized oligonucleotide can be oxidized with a variety of reagents to obtain either phosphate diester or other types of modified oligonucleotides.

REFERENCES:
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P. J. Garegg, et al., Tet. Let. 27: 4051-4054, 4055-4058 (1986).
B. C. Froehler et al., Nucl. Acid Res.,14: 5399-5407 (1986).
B. C. Froehler, Tet. Let. 27: 5575-5578 (1986).
B. C. Froehler and M. D. Matteucci, Tet. Let. 27: 469-472 (1986).
Garegg et al (II), Chemical Scripta, vol. 26, pp. 59-62, 1985.
Garegg et al (III), Chemica Scripta, vol. 25, pp. 280-282, 1985.
Nemer et al (I)., Tetrahedron Letters, vol. 21, pp. 4149-4152, 4153-4154 (1980).

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