Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1996-01-23
1998-01-13
Kunz, Gary L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 253, C07H 102, C07H 2104
Patent
active
057081611
ABSTRACT:
Inter alia, a process for the production of a nucleoside phosphorothioate derivative corresponding to the following general formula (I): ##STR1## characterized in that it comprises reacting a salt of a nucleoside H-phosphonate corresponding to the following general formula (II): ##STR2## with a thiol transfer agent corresponding to the following general formula (III):
REFERENCES:
Harpp and Beck, "The Preparation of N-(Alkyl and Arylsulfinyl)-Phthalimides. A New Class of Sulfinyl-Transfer Reagents," Tetrahedron Letters, 52: 5313-5316 (Dec. 1972).
Rao et al., "Dibenzoyl Tetrasulphide -A Rapid Sulphur Transfer Agent in the Synthesis of Phosphorothioate Analogues of Oligonucleotides," Tetrahedron Letters, 33(33): 4839-4842 (Aug. 11, 1992).
Reese et al., "Action of Toluene-p-thiol and Triethylamine on Fully Protected Thymidylyl-(3'.fwdarw.5')-thymidine. Possible Occurrence of Thiolate Ion-promoted Internucleotide Cleavage in the Synthesis of Oligonucleotides by the Phosphotriester Approach," J. Chem. Soc. Perkin Trans., I: 2451-2455 (1981).
Schaller et al., "Studies on Polynucleotides. XXIV The Stepwise Synthesis of Specific Deoxyribopolynucleotides (4). Protected Derivatives of Deoxyribonucleosides and New Syntheses of Deoxyribonucleoside-3' Phosphates," J. Am. Chem. Soc., 85: 3821-3827 (1963).
Sinha, N. D., "Large-Scale Oligonucleotide Synthesis Using the Solid-Phase Approach," (Chapter 18) Methods in Molecular Biology, vol. 20: Protocols for Oligonucleotides and Analogs, Ed. S. Agrawal, Humana Press, Inc. Totowa, NJ, pp. 437-463 (1993).
Stec and Wilk, "Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s," Angew. Chem. Int. Ed. Engl., 33:709-722 (1994).
Zhao Zhengyun, "Studies in the Chemistry of the Thio-Analogues of Nucleotides and Oligonucleotides," Thesis, University of London, King's College, pp. 181-182, (Jul. 1993).
Zon and Stec, "Phosphorothioate oligonucleotides," (Chapter 4) Oligonucleotides and Analogues -A Practical Approach, Ed. F. Eckstein, IRL Press, Oxford, pp. 87-108 (1991).
Zon, G., "Oligonucleoside Phosphorothioates," (Chapter 8) Methods in Molecular Biology, vol. 20: Protocols for Oligonucleotides and Analogs, Ed. S. Agrawal, Humana Press, Inc., Totowa, NJ, pp. 165-189 (1993).
Bauer and Welsh, "Addition of Thiourea to Acrylonitrile and Acrylamides," J. Org. Chem., 26: 1443-1445 (May 1961).
Beaucage, S. L., "Oligodeoxyribonucleotides Synthesis: Phosphoramidite Approach," Methods in Molecular Biology, vol. 20: Protocols for Oligonucleotides and Analogs, Ed. S. Agrawal, Humana Press, Inc., Totowa, NJ, pp. 33-61 (1993).
Behforouz and Kerwood, "Alkyl and Aryl Sulfenimides," J. Org. Chem., 34(1): 51-55 (Jan. 1969).
Benseler and McLaughlin, "An Improved Procedure for the Protection of 2'-Deoxyguanosine," Synthesis: 45-46 (Jan. 1986).
Burgers and Eckstein, "Diastereomers of 5'-O-Adenosyl 3'-O-Uridyl Phosphorothioate: Chemical Synthesis and Enzymatic Properties," Biochemistry, 18(4): 592-596 (1979).
Chattopadhyaya and Reese, "The 9-Phenylxanthen-9-yl Protecting Group," J.C.S. Chem. Comm.: 639-640 (1978).
Christodoulou and Reese, "Dealkylation of Nucleoside Arylmethyl 2-Chlorophenyl Phosphates: the 2,4-Dinitrobenzyl Protecting Group," Tetrahedron Letters, 24(9): 951-954 (1983).
Cohn and Friedlander, "UeberO-p-Dinitrobenzaldehyd," Ber., 35: 1265-1267 (1902).
Cosstick and Williams, "An approach to the stereoselective synthesis of Sp-dinucleoside phosphorothioates using phosphotriester chemistry," Nucleic Acids Research, 15(23): 9921-9932 (1987).
Dreef et al., "A Convenient Approach Towards the Conversion of H-Phosphonate and H-Phosphonothioate Diesters into Phosphoro-(di)thioate Derivatives," Synlett (Letters): 481-483 (Aug. 1990).
Froehler et al., "Synthesis of DNA via deoxynucleoside H-phosphonate intermediates," Nucleic Acid Research, 14(13): 5399-5407 (1986).
Ghosh et al., "Evaluation of some properties of a phosphorod ithioate oligodeoxyribonucleotide for antisense application," Nucleic Acids Research, 21(24): 5761-5766 (1993).
Horn, W. J., "Researches on Pyrimidines. XCI. Alkylation of 2-Mercapto-Pyrimidines," J. Am. Chem. Soc, 43: 2603-2611 (1921).
Horwitz et al., "Nucleosides. II. 5'-O-Mesylthymidine and 3'-O-Mesylthymidine," J. Org. Chem., 27: 3300-3302 (1962).
Jones et al., "Synthesis of the 3'-Terminal Decaribonucleoside Nonaphosphate of Yeast Alanine Transfer Ribonucleic Acid," Tetrahedron, 36: 3075-3085 (1980).
Kamimura et al., "Synthesis of a Dodecaribonucleotide, GUAUCAAUAAUG, by Use of `Fully` Protected Ribonucleotide Building Blocks," J. Am. Chem. Soc., 106(16): 4552-4557 (1984).
Kemal et al., "Use of 2,5-Dichlorophenyl Phosphorodichloridothioate in the Synthesis of Diasteroisomeric Dinucleoside Phosphorothioates," J. Chem. Soc. Chem. Communo.: 591-593 (1983).
Lesnikowski and Jaworska, "Studies on Stereospecific Formation of P-Chiral Internucleotide Linkage. Synthesis of (Rp,Rp)-and (Sp,Sp)-Thymidyly(3',5')Thymidyly(3',5')Thymidine Di(O,O-phosphorothioate) Using 2-Nitrobenzyl Group as New S-Protection," Tetrahedron Letters, 30(29): 3821-3824 (1989).
Miller, B., "Ease of Displacement of Thiol and Oxide Anions from Methyl Groups: Carbon Basicities of Anions of Oxygen and Sulphur," Proc. Chem. Soc.: 303 (Sep. 1962).
Muller and Roth, "A New Synthesis of Thiophosphoric Acid Esters with a C-S-P Bond," Tetrahedron Letters, 31(4): 501-502 (1990).
Nielsen et al., "Synthesis and Characterization of Dinucleoside Phosphorodithioates," Tetrahedron Letters, 29(24): 2911-2914 (1988).
Pant and Noltes, "The Reaction of Lead Bisthiolates with N-Halosuccinimides," Inorg. Nucl. Chem. Letters, 7(1): 63-66 (1971).
Porritt and Reese, "Use of the 2,4-Dinitrobenzyl Protecting Group in the Synthesis of Phosphorodithioate Analogues of Oligodeoxyribonucleotides," Tetrahedron Letters, 31(9): 1319-1322 (1990).
Rao and Reese, "Synthesis of cyclic oligodeosyribonucleotides via the `filtration` approach," Nucleic Acids Research, 17(20): 8221-8239 (1989).
Reese, C. B., "The Chemical Synthesis of Oligo-and Poly-Nucleotides by the Phosphotriester Approach," Tetrahedron (Report No. 56), 34: 3143-3179 (1978).
Reese and Skone, "The protection of Thymine and Guanine Residues in Oligodeoxyribonucleotide Synthesis," J. Chem. Soc. Perkin Trans., I: 1263-1271 (1984).
Reese and Pei-Zhuo, "Phosphotriester Approach to the Synthesis of Oligonucleotides: A Reappraisal," J. Chem. Soc. Perkin Trans., I: 2291-2301 (1993).
King's College London
Kunz Gary L.
Lauder Leona L.
LandOfFree
Nucleoside phosphorothioate derivatives, synthesis and use there does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Nucleoside phosphorothioate derivatives, synthesis and use there, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Nucleoside phosphorothioate derivatives, synthesis and use there will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-327899