Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1997-10-09
1999-08-31
Kunz, Gary L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 2534, 558 81, 568 12, 568 16, C07H 2100, C07H 102, C07F 96584
Patent
active
059455217
ABSTRACT:
Methods and intermediates for the preparation of oligomers containing diastereomerically enriched phosphorothioate linkages are disclosed.
REFERENCES:
patent: Re34069 (1992-09-01), Koster et al.
patent: 3846374 (1974-11-01), Farley et al.
patent: 4458066 (1984-07-01), Caruthers et al.
patent: 4500707 (1985-02-01), Caruthers et al.
patent: 4668777 (1987-05-01), Caruthers et al.
patent: 4725677 (1988-02-01), Koster et al.
patent: 4973679 (1990-11-01), Caruthers et al.
patent: 5132418 (1992-07-01), Caruthers et al.
patent: 5646267 (1997-07-01), Stec et al.
Stec et al. Nucl. Acids Res. 19(21): 5883-5888, 1991.
Bielinska, A. et al., "Regulation of gene expression with double-stranded phosphorothioate oligonucleotides", Science, 1990, 250, 997-1000.
Brody, R. et al., "Stereochemical course of nucleotidyl catalyzed by bacteriophage T7 induced DNA polymerase", Biochem., 1982, 21, 2570-2572.
Brody, R. et al., "Unambiguous determination of the sterochemistry of nucleotidyl transfer catalyzed by DNA polymerase I from Escherichia coli", Biochemistry, 1981, 20, 1245-1252.
Bryant, F. et al., "Stereochemical course of the reaction catalyzed by 5'-nucleotide phosphodiesterase from snake venom", Biochem., 1979, 2825-2628.
Burgers, P. et al., "A study of the mechanism of DNA polymerase I from escherichia coli with diastereomeric phosphorothioate analogs of deoxyadenosine triphosphate", J. Biol. Chem., 1979, 254(15), 6889-6893.
Burgers, P. et al., "Absolute configuration of the diastereomers of adenosine 5'-O-(1-thiotriphosphate): Consequences for the stereochemistry of polymerization by DNA-dependent RNA polymerase from Escherichia coli", Proc. Natl. Acad. Sci. USA, 1978, 75(10), 4798-4800.
Cruse et al., "Chiral Phosphorothioate Analogues of B-DNA", J. Mol. Biol., 1986, 192, 891-905.
Eckstein, F. et al., "Assignment of Resonances in the Phosphorus-31 Nuclear Substitution", Biochem., 1983, 22, 4546-4550.
Fujii et al., "Acylphosphonates. 7..sup.1 A New Method for Stereospecific and Stereoselective Generation of Dideoxyribonucleoside Phosphorothioates via the Acylphosphonate Intermediates", Tetrahedron, 1987, 43, 3395-3407.
Gupta et al., "Template-Primer-Dependent Turnover of (Sp)-dATP S by T4 DNA Polymerase", J. Biol. Chem., 1982, 257, 7689-7692.
Hall, G. et al., "Platinum(II) Complexes of P(III) Cyclophosphamide Derivatives", Phosphorus & Sulfur, 1979, 7, 235-240.
Huang, Y. et al., "Study of the Conformation Equilibria of 2-Z-Methyl-1,3,2-oxazaphosphorinanes. Steric and Stereoelectronic Influences on the Orientation of the Me2N Substituent on Three-Coordinate Phosphorous", J. Org. Chem., 1995, 60, 4767-4773.
Iyer, R. 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, 4693-4699.
Iyer, R. 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, 1253-1254.
Jager, A. et al., "Oligonucleotide N-alkylphosphoramidates: Synthesis and binding to polynucleotides", Biochem., 1988, 27, 7237-7246.
Jin, Y. et al., "A Stereoselective Synthesis of Dinucleotide Phosphorothioates, Using Chiral Phosphoramidites as Intermediates", Tetra. Lett., 1996, 37, 973-976.
Kamer et al., "An Efficient Approach Toward the Synthesis of Phosphorothioate Diesters Via the Schonberg Reaction", Tetra. Lett., 1989, 30, 6757-6760.
Koole, L.H. et al., "Enhanced stability of a Watson & Crick DNA duplex structure by methylation jof the phosphate groups in one strand", Proc. K. Ned. Acad. Wet., 1987, 90(1), 41-46.
Letsinger et al., "Effects of pendant groups at phosphorus on binding properties of d-ApA analogues", Nucl. Acids Res., 1986, 14, 3487-3490.
Marsault, E. et al., "Diasterioselective Synthesis of Phosphite Triesters Through a New Bicyclic Intermediate", Tetra. Lett., 1996, 37, 977-980.
Miller, P.S. et al., "Biochemical and Biological Effects of Nonionic Nucleic Acid Methylphosphonates", Biochem., 1981, 20, 1874-1880.
Niewiarowski, W. et al., "Diastereomers of Thymidine 3'O-(Methanephosphono-thioate): Synthesis, Absolute Configuration and Reaction with 3'-methoxyacetylthymidine Under Conditions of Triester Approach to Oligonucleotide Synthesis", Acta Biochim. Polonia, 1987, 34, 217-231.
Nifantyev, E.E. et al., "1,3,2-Oxazaphosphorinanes in Rhodium (I) Complexes", J. Organometallic Chem., 1987, 336, 237-247.
Nuretdinov, I. et al., "Nuclear Quadrupole Resonance of Chlorides & Amides of Phosphorus (III) Cyclic Acids", Chem. Abstrts., 1979, 90, 612.
Rao et al., "Dibenzoyl Tetrasulphide- A Rapid Sulphur Transfer in the Synthesis of Phosphorothioate Analoques of Oligonucleotides", Tetra. Lett., 1992, 33(33), 4839-4842.
Romaniuk, P. J. and Eckstein, F., "A study of the mechanism of t4 DNA polymerase with diasteromeric phosphorothioate analogues of deoxyadenosine triphosphate", Biol. Chem., 1982, 257(13), 7684-7688.
Stec, W.J., "Stereospecific synthesis of oligonucleotide p-chiral analogues", Pol. Acad. Sci., Jun. 18-21, 1989.
Stec, W. et al., "Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s", Angew. Chem. Int. Ed. Engl., 1994, 33, 709-722.
Stec et al., "Reversed-phase High-performance Liquid Chromatographic Separation of Diastereomeric Phosphorothioate Analogues of Oligodeoxyribonucleotides and Other Backbone-Modified Congeners of DNA", J. Chromatography, 1985, 326, 263-280.
Takahata, H. et al., "Concise Syntheses of Natural .gamma.-Butyrolactones, (+)-trans-Whisky Lactone, (+)-trans-Cognac Lactone, (-)-Methylenolactocin, (+)-Nephrosteranic Acid, and (+)-Roccellaric Acid Using Novel Chiral Butenolide Synthons", J. Org. Chem., 1995, 60, 5628-5633.
Ueda, T. et al., "Phosphorothioate-containing RNAs show mRNA activity in the prokaryotic translation systems in vitro", Nucl. Acids Res., 1991, 19, 547-552.
Vu, H. et al., "Internucleotide Phosphate Sulfurization with Tetraethylthiuram Disulfide, Phosphorothioate Oligonucleotide Synthesis via Phosphoramidite Chemistry", Tetra. Lett., 1991, 32(26), 3005-3008.
Wu, H. et al., "Inhibition of in vitro transcription by specific double stranded oligodeoxyribonucleotides", Gene, 1990, 89, 203-209.
Xin, Z. et al., "Diastereoselective Synthesis of Phosphite Triesters", Tetra. Lett., 1996, 37, 969-972.
Jin Yi
Just George
Marsault Eric
Xin Zhili
Kunz Gary L.
McGill University
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