Sulfurization of phosphorus-containing compounds

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Chemical aftertreatment – e.g. – acylation – methylation – etc.

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530330, 530331, 530404, 536 253, 536 2534, 548129, 548130, 558122, 558124, C07F 902, C07F 100, C07F 1107

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active

058521682

ABSTRACT:
The present invention provides a method for sulfurizing a phosphorus-containing compound, such as a trivalent phosphorus compound, using a disulfide-containing five-membered heterocycle.

REFERENCES:
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 5003097 (1991-03-01), Beaucage et al.
patent: 5395928 (1995-03-01), Bergot
Xu, Q. et al., "Use of 1,2,4-dithiazolidine-3,5-dione (DtsNH) and 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH) for synthesis of phosphorothioate-containing oligodeoxyribonucleotides," Nucleic Acids Research, 24(9), 1602-1607 (1996).
Xu, Q. et al., "Efficient introduction of phosphorothioates into RNA oligonucleotides by 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH)," Nucleic Acids Research, 24(18), 3643-3644 (1996).
Xu, Q. et al., "N-Dithiasuccinoyl (DTS)-Amines: Novel Sulfurizing Reagents for the Solid-Phase Preparation of Thiophosphopeptides and Oligodeoxyribonucleodside Phosphorothioates," Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries, Ed., R. Epton Fourth International Symposium, Sep. 12-16, 1995, Edinburgh, Scotland, U.K. (1996).
N.I.H. Grant No. 28934 Abstract (1986).
N.I.H. Grant No. 42722 Abstract (1992).
N.I.H. Grant No. 43552 Abstract (1989).
N.I.H. Grant No. 49928 Abstract (1992).
N.S.F. Grant No. CHE-9500992 (1995).
Agrawal et al., "Efficient Synthesis of Oligoribonucleotide and its Phosporothioate Analogue Using H-Phosphonate Approach," Tetrahedron Lett., 31(52) 7541-7544 (1990).
Ausserer et al., "High-Resolution Analysis and Purification of Synthetic Oligonucleotides with Strong Anion-Exchange HPLC," Biotechniques, 19(1) 136-139 (1995).
Barany et al., "A General Strategy for Elaboration of the Dithiocarbonyl Functionality -(C=0)SS-: Application to the Synthesis of Bis(chlorocarbonyl)disculfane and Related Derivatives of Thiocarbonic Acids," J. Org. Chem., 48(24) 4750-4761 (1983).
Barelli et al., "Potent inhibition of endopeptidase 24.16 and endopeptidase 24.15 by the phosphonamide peptide N-(phenylethylphosphonyl)-Gly-L-Pro-Laminohexanoicacid," Biochem. J., 287 (Part 2) 621-625 (1992).
Bongartz et al., "Improved Biological activity of antisense oligonucleotides conjugated to a fusogenic peptide," Nucleic Acids Research, 22(22) 4681-4688 (1994).
Cao et al., "Layered Metal Phosphates and Phosphonates: From Crystals to Monolayers," Acc. Chem. Res., 25(9) 420-427 (1992).
Connolly et al., "Synthesis and Characterization of an Octanucleotide Containing the EcoRI Recognition Sequence with a Phosphorothioate Group at the Cleavage Site," Biochemistry, 23:3443-3453 (1984).
de Bont et al., "Solid-Phase Synthesis of .omicron.-Phosphorothioylserine- and -threonine-Containing Peptides as Well as of .omicron.-Phosphoserine- and -threonine-Containing Peptides," J. Org. Chem., 58 1309-1317 (1993).
Eckstein et al., "Phosphorothioates in molecular biology," TIBS, 14 97-100 (1989).
Efimov et al., "New efficient sulfurizing reagents for the preparation of oligodeoxyribonucleotide phosphorothioate analogues," Nucleic Acids Research, 23(20) 4029-4033 (1995).
Fernandez et al., "Synthesis of Phosphonate and Thiophosphonate Esters and Amides from Hydrogen-Phosphinates by a Novel One-Pot Activation-Coupling Oxidation Procedure," J.Org. Chem., 60 7390-7391 (1995).
Fidanza et al., "Site-Specific Labeling of DNA Sequences Containing Phosphorothioate Diesters," J. Am. Chem. Soc., 114 5509-5517 (1992).
Froehler, "Deoxynucleoside H-Phosphonate Diester Intermediates in the Synthesis of Internucleotide Phosphate Analogues," Tetrahedron Lett., 27(46) 5575-5578 (1986).
Garegg et al., "Formation of Internucleotidic Bonds via Phosphonate Intermediates," Chemica Scripta, 25 280-282 (1985).
Harris, "The Reactions of Sulfenyl chlorides with Thionocarbamates," Sulfenyl Chlorides with Thionocarbomates 82 155-158 (1960).
Iyer 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., 55 4693-4699 (1990).
Kaplan et al., "Synthesis and Evaluation of an Inhibitor of Caroxypeptidase A with a K.sub.i Value in the Femtomolar Range," Biochemistry, 30(33) 8165-8170 (1991).
Kitas et al., "Chemical synthesis of .omicron.-thiophosphotyrosyl peptides," Int. J. Peptide Protein, 43 146-153 (1994).
Koziolkiewicz et al., "Application of Phosphate-Backbone-Modified Oligonucleotides in the Studies on EcoRI Endonuclease Mechanism of Action," Biochemistry, 31 9460-9466 (1992).
Maiti et al., "Phosphorus-Containing Polymers," Prog. Polym. Sci., 18(2) 227-261 (1993).
Martin et al., "General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-glycerols," J. Org. Chem., 59(17) 4805-4820 (1994).
Martin et al., "Design, Synthesis, and Evaluation of Phospholipid Analogues as Inhibitors of the Bacertial Phospholipase C from Bacilus cereus," J. Org. Chem., 59(17) 4821-4831 (1994).
Martin et al., "General and Efficient Route to Phosphorodithioate Analogues of Naturally Occurring Lipids," J. Org. Chem., 58(22) 5897-5899 (1993).
Milligan et al., "Determination of RNA-Protein Contacts Using Thiophosphate Substitutions," Biochemistry, 28 2849-2855 (1989).
Moore et al., "Evidence for two active sites in the spliceosome provided by sterochemistry of pre-mRNA splicing," Nature, 365(1993).
Morgan et al., "Differential Binding Energy: A Detailed Evaluation of the Influence of the Hydrogen-Bonding and Hydrophobic Groups on the Inhibition of Thermolysin by Phosphorus-Containing Inhibitors," J. Am. Chem. Soc., 113(1) 297-307 (1991).
Musier-Forsyth et al., "Acceptor Helix Interactions in a Class II tRNA Synthetase: Photoaffinity Cross-Linking of an RNA Miniduplex Substrate," Biochemistry, 33 773-779 (1994).
Ottinger et al., "Synthesis of Phosphotyrosine-Containing Peptides and Their Use as Substrates for Protein Tyrosine Phosphates," Biochemistry, 32(16) 4354-4361 (1993).
Rao et al., "Dibenzoyl Tetrasulphide--Rapid Sulphur Transfer Agent in the Synthesis of Phosphorothioate Analogues of Oligonucleotides," Tetrahedron Lett., 33(33) 4839-4842 (1992).
Rao et al., "Solid Phase Synthesis of Phosphorothioate Oligonucleotides Using Benzyltriethylammonium Tetrathiomolybdate as a Rapid Sulfur Transfer Reagent," Tetrahedron Lett., 35(36) 6741-6744 (1994).
Roelen et al., "A study on the use of phenylacetyl disulfide in the solid-phase synthesis of oligodeoxynucleoside phosphorothioates," Recl. Trav. Chim. Pays-Bas, 110 325-331 (1991).
Slomczynska et al., "Efficient Synthesis of 1,2,4-Dithiazolidine-3,5-diones (Dithiasuccinoyl-amines) and Observations on Formation of 1,2,4-Thiadiazolidine-3,5-diones by Related Chemistry," J. Heterocyclic Chem., 21 241-246 (1984).
Sproat et al., "An Efficient Method for the Isolation and Purification of Oligoribonucleotides," Nucleosides and Nucleotides, 14(1&2) 255-273 (1995).
Stec et al., "Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s," Agnew. Chem. Int. Ed. Engl., 33(7) 709-722 (1994).
Stec et al., "Automated Solid-Phase Synthesis, Separation, and Sterochemistry of Phosphorothioate Analogues of Oligodeoxyribonucleotides," J. Am. Chem., 106 6077-6079 (1984).
Stec et al., "Bis(O,O-Diisopropoxy Phosphinothioyl) Disulfide--A Highly Efficient Sulfurizing Reagent for Cost-Effective Synthesis of Oligo(Nucleoside Phosphorothioate)s" Tetrahedron Lett., 34(33) 5317-5320 (1993).
Tegge, "Solid-phase syntheses of phosphorylated and thiophosphorylated peptides related to an EGFR sequence," Int. J. Peptide Protein Res., 43 448-453 (1994).
Uhlman et al., "Antisense Oligonucleotides: A New Therapeutic Principle," Chemical Reviews, 90(4) 544-584 (1990).
Vu et al., "Internucleotide Phosphite Sulfurization with Tetraethylthiuram Disulfide Phosphorothioate Oligonucleotide Synthesis Via Phosphoramidite Oligonucleotide Synthesis Via Phosphoramidite Chemistry" Tetrahedron Lett., 32(26) 3005-3008 (1991).
Vyle et al., "New Methods for Synthesis of 3'-S-Phosphorothiolate Internucleoside Linkages," Tetrahedron Lett., 33(21) 3017-3020 (1992).
Wagner, "Gene inhibition using antisense oligodeoxynucleotides," Nature, 372 333-335 (1994).
Wheeler et al., "On the

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