Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2005-08-17
2010-12-14
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C540S454000, C564S169000
Reexamination Certificate
active
07851658
ABSTRACT:
A novel palladium-mediated carbon-carbon bond forming reaction has been discovered using DNA-templated chemistry. The inventive reaction involves the palladium-mediated coupling of a terminal alkyne with an alkene to form an enone. A catalytic amount of palladium may be used in the reaction if an oxidant is present. The reactions is also compatible with a variety of organic solvent as well as aqueous solution. Both intermolecular and intramolecular reactions have been demonstrated. This novel carbon-carbon bond forming reaction is particularly useful in the synthesis of macrocycles. Kits, reagents, catalysts, solvents, oxidants, salts, acids, instructions, and other materials useful in the practice of the inventive reaction are also provided.
REFERENCES:
patent: 4835312 (1989-05-01), Itoh et al.
patent: 5457111 (1995-10-01), Luly et al.
patent: 5677467 (1997-10-01), Hoye et al.
patent: 5880280 (1999-03-01), Organ et al.
patent: 6368808 (2002-04-01), Sato et al.
patent: 6387901 (2002-05-01), Chupak
patent: 6700025 (2004-03-01), Moriarty et al.
patent: 6774229 (2004-08-01), Mueller et al.
patent: 2004/0018042 (2004-01-01), Smith et al.
Chiusoli et al, Gazzetta Chimica Italiana, 1987, 117(1), 695-700.
Breslow, et al., “Biomimetric Chemistry and Artificial Enzymes: Catalysis by Design.”Acc. Chem. Res. 28: 146-153, 1995.
Burrows, et al., “Oxidative Nucleobase Modifications Leading to Strand Scisson”Chem. Rev. 98: 1109-1152, 1998.
Calderone, et al., “Directing Otherwise Incompatible Reactions in a Single Solution by Using DNA-Templated Organic Synthesis.”Angew. Chem. Int. Ed. 41: 4104-8, 2002.
Corey, et al.,J. Org. Chem. 51: 1925-1926, 1986.
Cotarca, et al.,Synthesis328-332, 1997.
Delia, et al.,Heterocycles35: 1397-1410, 1993.
Evans, et al., “Proton-Activated Fluorescence As a Tool for Simultaneous Screening of Combinatorial Chemical Reactions.”Curr. Opin. Chem. Biol. 6: 333-338, 2002.
Gartner, et al., “The Generality of DNA-Templated Synthesis As a Basis for Evolving Non-Natural Small Molecules”J. Am. Chem. Soc. 123: 6961-3, 2001.
Gartner, et al., “Expanding the Reaction Scope of DNA-Templated Synthesis.”Angew Chem. Int. Ed. 41: 1796-1800, 2002.
Heck, et al., “Palladium-Catalyzed Vinylation of Organic Halides”Org. React. 27: 345, 1982.
Joyce, et al., “Directed Evolution of Nucleic Acid Enzymes”Annu. Rev. Biochem. 73: 791-836, 2004.
Kohli, et al., Biomimetric Synthesis and Optimization of Cyclic Peptide Antibiotics.Nature418: 658-61, 2002.
Kusumoto, et al.,Bull. Chem. Soc. Jpn. 59: 1296-1298, 1986.
Li, et al., “Stereoselectivity in DNA-Templated Organic Synthesis and Its Origins.”J. Am. Chem. Soc. 125: 10188-9, 2003.
Lober, et al., “Palladium-Catalyzed Hydroamination of 1,3-Dienes: A Coloimetric Assay and Enantioselective Additions.”J. Am. Chem. Soc. 123: 4366-7, 2001.
Miyaura, et al., “Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds.”Chem. Rev. 95: 2457-2483, 1995.
Oku, et al.,J. Org. Chem. 65: 1899-1906, 200.
Reetz, et al., “Combinatorial and Evolution-Based Methods in the Creation of Anantioselective Catalysts”Angew. Chem. Int. Ed. 40: 284-310, 2001.
Rosenbaum, et al., “Efficient and Sequence-Specific DNA-Templated Polymerization of Peptide Nucleic Acid Aldehydes.”J. Am. Chem. Soc. 125: 13924-5, 2003.
Rostovtsev, et al., “A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective ‘Ligation’ of Azides and Terminal Alkynes.”Angew. Chem. Int. Ed. 41: 2596-9, 2002.
Schultz, et al.,. “Completing the Circle.”Nature418: 485, 2002.
Smidt, et al.,Angew. Chem. 71: 176-182, 1959.
Smidt, et al.,Angew Chem74: 93-102, 1962.
Stambuli, et al., “Recent Advances in the Discovery of Organometallic Catalysts Using High-Throughput Screening Assays”Curr. Opin. Chem. Biol. 7: 420-426, 2003.
Stambuli, et al., “Screening of homogenous Catalysts by Fluorescence Resonance Energy Transfer. Identification of Catalysts for Room-Temperature Heck Reactions.”J. Am. Chem. Soc. 123: 2677-8, 2001.
Staunton, et al., “Polyketide Biosynthesis: A Millennium Review.”Nat. Prod. Rep. 18: 380-416, 2001.
Taylor, et al, “Thermographic Selection of Effective Catalysts From an Encoded Polymer-Bound Library.”Science280: 267-70, 1998.
Wadsworth, et al., “Utility of Phosphate Carbanions in Olefin Synthesis”J. Am. Chem. 83: 1733-8, 1961.
Wang, et al., “Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3+2] Cycloaddition.”J. Am. Chem. Soc. 125: 3192-3, 2003.
Wilson, et al., “In Vitro Selection of Functional Nucleic Acids.”Annu. Rev. Biochem. 68: 611-647, 1999.
International Search Report and Written Opinion for PCT/US2005/029294 mailed Aug. 2, 2007.
International Preliminary Report on Patentability for PCT/US2005/029294 mailed Sep. 7, 2007.
Kanan et al., Reaction discovery enabled by DNA-templated synthesis and in vitro selection. Nature. Sep. 30, 2004;431(7008):545-9. 30;431(7008):545-9.
Kanan Matthew W.
Liu David R.
Rozenman Mary M.
Baker C. Hunter
Kumar Shailendra
President and Fellows of Harvard College
Wolf Greenfield & Sacks P.C.
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