Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Chemical aftertreatment – e.g. – acylation – methylation – etc.
Patent
1996-04-30
1998-12-22
Raymond, Richard L.
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Chemical aftertreatment, e.g., acylation, methylation, etc.
530330, 530331, 530404, 536 253, 536 2534, 548129, 548130, 558122, 558124, C07F 902, C07F 100, C07F 1107
Patent
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
Barany George
Chen Lin
Hammer Robert P.
Musier-Forsyth Karin
Xu Qinghong
Raymond Richard L.
Regents of the University of Minesota
The Board of Supervisors of LA State University
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