Synthesis of sulfurized oligonucleotides

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S025300, C536S025330, C568S022000

Reexamination Certificate

active

07378516

ABSTRACT:
Methods for the formation of sulfurized oligonucleotides are provided. The methods allow for the formation of phosphorothioate linkages in the oligonucleotides or derivatives, without the need for complex solvent mixtures and repeated washing or solvent changes. Oligonucleotides having from about 8, and up to about 50, nucleotides can be sulfurized according to the methods of the invention with higher yields than have been previously reported.

REFERENCES:
patent: 3923763 (1975-12-01), Edmondson
patent: 4245033 (1981-01-01), Eida et al.
patent: 5264566 (1993-11-01), Froehler et al.
patent: 5902881 (1999-05-01), Cheruvallath et al.
patent: 6114519 (2000-09-01), Cole et al.
patent: 6242591 (2001-06-01), Cole et al.
patent: 7227015 (2007-06-01), Cole et al.
patent: 2003/0212267 (2003-11-01), Cole et al.
patent: 8902521 (1989-10-01), None
patent: 8902521 (1991-05-01), None
patent: WO91/16331 (1991-10-01), None
patent: WO93/13118 (1993-07-01), None
patent: WO96/06853 (1996-03-01), None
patent: WO96/09406 (1996-03-01), None
patent: WO 99/19340 (1999-04-01), None
patent: WO01/51502 (2001-07-01), None
Zhang et al.(I), “Synthesis and Properties of Novel Thiono Triester Modified Antisense Oligodeoxynucleotide Phosphorothioates,” Bioorganic & Medicinal Chem. Letters, 5(15), 1735-1740 (Aug. 3, 1995).
Zhang et al. (II), “Thiono Triester Modified Antisense Oligonucleotides for Inhibition of Human Cytomegalovirus In Vitro,” Bioorganic & Medicinal Chem. Letters, 6(16), 1911-1916 (Aug. 20, 1996).
Bokarev et al., “Synthesis of Bis(Alkyl Xanthyl) Trisulfides,” Izv. Akad. Nauk SSSR, Ser. Khim., 1964(12), 2175-2182; Chemical Abstracts, 62(7), Abstr. No. 7631d (Mar. 29, 1965); only Abstract supplied.
Scholl et al., “Novel Symmetrical and Mixed Carbamoyl and Amino Polysulfanes by Reactions of (Alkoxydichloromethyl)polysulfuranyl Substrates with N-Methylaniline,” Journal of Organic Chemistry, 51(10), 1866-1881 (1986).
Barany et al., “A General Strategy for Elaboration of the Dithiocarbonyl Functionality, -(C=O)SS-: Application to the Synthesis of Bis(chlorocarbonyl)disulfane and . . . ,” Journal of Organic Chemistry, 48(24), 4750-4761 (Dec. 2, 1983).
Carey et al., Advanced Organic Chemistry, 3rd Ed., Part A: Structure and Mechanisms, Plenum Press, New York, NY, 1990, only pp. 473-475 supplied.
DeBont et al., “Solid-phase synthesis of O-phosphorothioylserine- and -threonine-containing peptides as well as O-phosphoserine- and -threonine-containing peptides”,J. Org. Chem., 1993, 58(6), 1309-1317.
Dreef, C.E. et al., “An expeditious synthesis of biologically important myo-inositol phosphorothioates”,Bioorg. Med. Chem. Lett., 1991, 1(5), 239-242.
Iyer, R., Beaucage, Serge L. et al., “3H-1,2-benzodithiole-3-one 1,1-dioxide as an improved sulfurizing reagent in the solid-phase synthesis of oligodeoxyribonucleoside phosphorothiioates”,J. Am. Chem. Soc., 1990, 112, 1253-1255.
Iyer, R.P. et al., “The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1,1-Dioxide as a Sulfur-Transfer Reagent”,J. Org. Chem., 1990, 55(15), 4693-4699.
Kamer et al., “An Efficient Approach Toward the Synthesis of Phosphorothioate DiestersViathe Schönberg Reaction”,Tetra. Lett., 1989, 30(48), 6757-6760.
Kodomari et al., “A Convenient Synthesis of Bis[acyl] Disulfides using Phase-Transfer Catalysis”,Synthesis, 1981, 637-638.
Kozikowski, A.P. et al., “Tools for Cell Signaling: Synthesis of the 3-Phosphatase-Resistant 1,3,4,5-InsP4 Mimic, 1D-myo-Inositol 1,4,5-Triphosphate 3-Phosphorothioate”,J. Org. Chem., 1994, 58(9), 2279-2281.
Lozano, J.I. et al., “Electrosynthesis of 2-benzhydrylidene-4,4-diphenyl-1, 3-oxathiolan-5-one: the reaction pathway”,Tetrahedron, 1996, 52(4), 1259-1266.
Roelen et al., “A study on the use of phenylacetyl disulfide in the solid-phase synthesis of oligodeoxynucleoside phosphorothioates”,Rech. Trav. Chim. Pays-Bas, 1991, 110, 325-331.
Wyrzykiewicz, T.K. et al., “Efficiency of sulfurization in the synthesis of oligodeoxyribonucleotide phosphorothioates utilizing various sulfurizing reagents”,Bioorg. Med. Chem. Lett., 1994, 4(12), 1519-1522.
Cheruvallath, Z. S. et al., “Sulfurization Efficiency in the Solution Phase Synthesis of Deoxyribonucleoside Phosphorothioates—Comparison of Sulfur Triethylamine with Various Sulfurizing Agents,”Nucleosides Nucleotides(1996) 15(9):1441-1445.
Kamer, P. C. J. et al., “An Efficient Approach Toward the Synthesis of Phosphorothioate Diestersviathe Schönberg Reaction,”Tetrahedron Lett. (1989) 30(48):6757-6760.
Roelen, H. C. P. F. et al., “A study on the use of phenylacetyl disulfide in the solid-phase synthesis of oligodeoxynucleoside phosphorothioates,”Recl. Trav. Chim. Pays-Bas(1991) 110:325-331. (Jul./Aug., 1991).
Wyrzykiewicz, T. K. et al., “Efficiency of Sulfurizaton in the Synthesis of Oligodeoxyribonucleotide Phosphorothioates Utilizing Various Sulfurizing Reagents,”Bioorg. Med. Chem. Lett. (1994) 4(12):1519-1522.
“Instrument Specific Safety,”Models 392 and 394 User's Safety Summary(1994) Applied Biosystems, Inc., p. 2-10. (Mar. 1994).
“Synthesizing Mixed Phosphorothioate and Phosphodiester Oligonucleotides,”User Bulletin 65(1991) Applied Biosystems, Inc., pp. UB65-1-UB65-12. (Oct. 1991).

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