Phosphoramidite activator for oligonucleotide synthesis

Details Phosphoramidite activator for oligonucleotide synthesis Phosphoramidite activator for oligonucleotide synthesis

2005-02-08

2008-03-04

Crane, L. E. (Department: 1623)

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

Organic compounds

Carbohydrates or derivatives

C548S251000, C548S355100

Reexamination Certificate

active

07339052

ABSTRACT:
The present invention provides an improved phosphoramidite activator comprising a solution of 5-benzylmercaptotetrazole in acetonitrile and N-alkyimidazole. Further provided are improved methods of oligonucleotide synthesis wherein a phosphoramidite activator comprising a solution of 5-benzylmercaptotetrazole in acetonitrile and N-alkyimidazole is used to prepare internucleoside linkages.

REFERENCES:
patent: 3687808 (1972-08-01), Merrigan et al.
patent: 5212295 (1993-05-01), Cook
patent: 5824793 (1998-10-01), Hirschbein et al.
patent: 6166197 (2000-12-01), Cook et al.
patent: 6274725 (2001-08-01), Sanghvi et al.
patent: 6642373 (2003-11-01), Monoharan et al.
patent: 7148219 (2006-12-01), Lou et al.
patent: 2003/0069410 (2003-04-01), Ravikumar
patent: 2006/0004069 (2006-01-01), Momose et al.
Noe and Kaufhold, “9 Chemistry of Antisense Oligonucleotides,” New Trends in Synthetic Medicinal Chemistry,Wiley-VCh, Weinheim, 2000, 261-347.
Applied BioSystems User's Manual for Models 392 and 394 DNA/RNA Synthesizers; Section 6 Chemistry for Automated DNA/RNA Synthesis (Mar. 1994).
http://www.eurogentec.be/ code/EN/what.asp?pk—id—what=85)—Feb. 8, 2005.
Claudia Hobartner et al. “The Synthesis of 2′-0-[Triisopropylsilyl)oxy] methly (TOM) Phosphoramidites of Methylated Ribonucleosides for Use in Automated RNA Solid-Phase Synthesis,” Monatshefte Fur Chemie 134, 851-873 (2003).
Chandra Vargeese, et al. “Efficient activiation of nucleoside phosphoramidites with 4,5-dicyanoimidazole during oligonucleotide synthesis,” 1046-1050 Nucleic Acids Research, 1998, vol. 26, No. 4.
www.glenres.com/GlenReports/GR10-1.pdf—Feb. 8, 2005.
Wagner et al., Nucleosides & Nucleotides, 1997, 17, pp. 1657-1660.
Bhan et al., Nucleosides & Nucleotides, 1997, 17, pp. 1195-1199.
X. Wu and S. Pitsch,Nucleic Acids Research1998, vol. 26, No. 19, pp. 4315-4323).
Ouchi, et al.,Drug Design and Discovery1992, vol. 9, pp. 93-105.
Ravasio, et al.,J. Org. Chem.1991, 56, pp. 4329-4333.
Secrist, et al., “Abstract 21, Program & Abstracts”, Tenth International Roundtable,Nucleosides, Nucleotides and their Biological Applications, Park City, Utah, Sep. 16-20, 1992.
Greene and Wuts,Protective Groups in Organic Synthesis, Chapter 7, 2d ed, John Wiley & Sons, New York, 1991.
Englisch et al.,Angewandte Chemie, International Edition 1991, vol. 30, No. 6, pp. 613-629.
Limbach, A., et al.,Nucleic Acids Research, 1994, vol. 22, No. 12, 2183-2196.
Alul, et al., Nucleic Acids Research 1991, vol. 19, No. 7, 1527-1532.
TentaGel Support, An Aminopolyethyleneglycol Derivatized Support (see, e.g., Wright, et al., Tetrahedron Letters 1993, vol. 34, No. 21, pp. 3373-3376.
M.J. Gait, “Oligonucleotide Synthesis, A Practical Approach”, IRL Press at Oxford University Press (1984, ISBN 0-904147-74-6).
S. Pitsch, et al. Helvetica Chimica Acta—vol. 84 (2001) pp. 3773-3795.
V. Serebryany and L. Beigelman, “An efficient preparation of protected ribonucleosides for phosphoramidite RNA Synthesis,” Tetrahedron Letters 43 (2002) pp. 1983-1985.
Welz R, et al “5-(Benzylmercapto)-1H-Tetrazole as Activator for 2'-0-TBDMS Phosphoramidite Building Blocks in RNA Synthesis” vol. 43, No. 5 pp. 795-797 dated Jan. 28, 2002 XP004332810.
Stutz Alfred, et al “Novel Fluoride-Labile Nucleobase-Protecting Groups for the Synthesis of 3'(2')-0-Amino-Acylated RNA Sequences” vol. 83, No. 9 pp. 2477-2503 dated 2000 XP002979645.

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