S-adenosyl-L-methionine analogs with extended activated...

Details S-adenosyl-L-methionine analogs with extended activated... S-adenosyl-L-methionine analogs with extended activated...

2011-08-30

2011-08-30

Crane, Lawrence E (Department: 1623)

Chemistry: molecular biology and microbiology

Measuring or testing process involving enzymes or...

Involving nucleic acid

C435S088000, C536S027310

Reexamination Certificate

active

08008007

ABSTRACT:
S-Adenosyl-L-methionine analogs of formula (I):are disclosed wherein R comprises a carbon-carbon double bond, carbon-sulfur double bond, carbon-nitrogen double bond, -a carbon-carbon triple bond, carbon-nitrogen triple bond or an aromatic carbocyclic or heterocyclic system in β-position to the sulfonium center, X{circle around (−)}is an organic or inorganic anion carrying one or more negative charges, Z is —CR1R2—, —O—, —S— or —NR3— and R1, R2and R3are independently selected from H, D and C1—C alkyl; as well as complexes with a methyltransferase, pharmaceutical compositions, methods for modifying a biomolecule, and methods for detecting sequences specific methylation of biomolecules.

REFERENCES:
patent: 2007/0264667 (2007-11-01), Gellibolian et al.
patent: 2009/0018101 (2009-01-01), Weinhold et al.
patent: 88/10315 (1988-12-01), None
patent: 89/09622 (1989-10-01), None
Brada et al., Early Alteration in Liver of Rats Fed 2-Fluorenylacetamide Investigated by L-Ethionine Probe, Chemico-Biological Interactions, 66(3-4), 287-295 (1988): in Search Notes (SRNT), see CAPLUS Answer 4 of 8.
International Search Report, PCT/EP2006/003463, Oct. 27, 2006.
Pljevaljcic et al., “Design of a New Fluorescent Cofactor for DNA Methyltransferases and Sequence-Specific Labeling of DNA,” J. Am. Chem. Soc. 125, (2003) pp. 3486-3492.
Pljevaljcic et al., “Sequence-Specific DNA Labeling U sing Methyltransferases,” Methods Mol. Biol. 283, (2004) pp. 145-161.
De La Haba et al., “S-Adenosylmethionine: The Relation of Configuration at the Sulfonium Center to Enzymatic Reactivity,” J. Am. Chem. Soc., (1959) vol. 81, pp. 3975-3980.
Stecher et al., “Biocatalytic Friedel-Crafts Alkylation using Non-natural Cofactors,” Angew. Chem. Int. Ed. 2009, 48, pp. 9546-9548.
Pljevaljcic et al., “Sequence-specific Methyltransferase-induced Labeling of DNA (SMILing DNA),” ChemBioChem 2004, 5, pp. 265-269.
Schlenk et al., “The S-n-Propyl Analogue of S-Adenosylmethionine,” Biochimica et Biophysica Acta, 385 (1975) pp. 312-323.
Schlenk, F., “Recent Studies of the Chemical Properties of Adenosylmethionine and Related Compounds,” Biochem, 1977, pp. 3-17.
Liu et al., “Peptide segment ligation strategy without use of protecting groups,” Proc. Natl. Acad. Sci, USA, Jul. 1994, vol. 91, pp. 6584-6588.
Dawson et al., “Synthesis of Proteins by Native Chemical Ligation,” Science, Nov. 4, 1994, vol. 266, pp. 776-779.
Lewis et al., “Click Chemistry In Situ: Acetylcholinesterase as a Reaction Vessel for the Selective Assembly of a Femtomolar Inhibitor from an Array of Building Blocks,” Angew. Chem. Int. Ed., 2002, 41, No. 6, pp. 1053-1057.
Saxon et al., “Cell Surface Engineering by a Modified Staudinger Reaction,” Science, Mar. 17, 2000, vol. 287, pp. 2007-2010.
Casalnuovo et al., “Palladium-Catalyzed Alkylations in Aqueous Media,” J. Am. Chem. Soc. 1990, 112, pp. 4324-4330.
Dibowski et al., “Bioconjugation of Peptides by Palladium-Catalyzed C-C Cross Coupling in Water,” Angew Chem. Int. Ed. 1998, 37, No. 4, pp. 476-478.
Bong et al., “Chemoselective Pd(0)-Catalyzed Peptide Coupling in Water,” Organic Letters, 2001, vol. 3, No. 16, pp. 2509-2511.
Devasher et al., “Aqueous-Phase, Palladium-Catalyzed Cross-Coupling of Aryl Bromides under Milder Conditions, Using Water-Soluble, Sterically Demanding Alkylphosphines,” J. Org. Chem. 2004, 69, pp. 7919-7927.
Porath et al., “Metal chelate affinity chromatography, a new approach to protein fractionation,” Nature, Dec. 18, 1975, vol. 258, pp. 598-599.
Porath J., “Immobilized Metal Ion Affinity Chromatography,” Protein Expression and Purification 3, (1992), pp. 263-281.
Hemdan et al., “Development of Immobilized Metal Affinity Chromatography: II. Interaction of Amino Acids with Immobilized Nickel Iminodiacetate,” Journal of Chromatography, 323 (1985) pp. 255-264.
Porath et al., “Cascade-mode multiaffinity chromatography: Fractionation of human serum proteins,” Journal of Chromatography, 550 (1991) pp. 751-764.
Schmidt et al., “The random peptide library-assisted engineering of a C-terminal affinity peptide, useful for the detection and purification of a functional Ig Fv fragment,” Protein Engineering, vol. 6, No. 1, 1993, pp. 109-122.
Kagan et al., “Widespread Occurrence of Three Sequence Motifs in Diverse S-Adenosylmethionine-Dependent Methyltransferases Suggests a Common Structure for These Enzymes,” Archives of Biochemistry and Biophysics, vol. 310, No. 2, May 1, 1994, pp. 417-427.
Walker et al., “Strand displacement amplification-an isothermal, in vitro DNA amplification technique,” Nucleic Acids Research, vol. 20, No. 7, 1992, pp. 1691-1696.
Galfre et al., “Preparation of Monoclonal Antibodies: Strategies and Procedures,” Methods in Enzymology, vol. 73, pp. 3-46, (1981).
Schier et al., “Efficient in vitro affinity maturation of phage antibodies using BIAcore guided selections,” Hum. Antibod. Hybridomas, 1996, vol. 7, 3, pp. 97-105.
Malmborg et al., “BIAcore as a tool in antibody engineering,” Journal of Immunological Methods, 183 (1995), pp. 7-13.
Ross et al., “A straightforward preparation of primary alkyl triflates and their utility in the synthesis of derivatives of ethidium,” J. Chem. Soc., Perkin Trans. 1, 2000, pp. 571-574.
Kumar et al., “DNA containing 4′-thio-2′-deoxycytidine inhibits methylation by Hhal methyltransferase,” Nucleic Acids Research, 1997, vol. 25, No. 14, pp. 2773-2783.
Kunkel T., “Rapid and efficient site-specific mutagenesis without phenotypic selection,” Proc. Natl. Acad. Sci. USA, vol. 82, Jan. 1985, pp. 488-492.
Kumar et al., “Purification, Crystallization, and Preliminary X-ray Diffraction Analysis of M.Hhal-AdoMet Complex,” Biochemistry 1992, 31, pp. 8648-8653.
Klimasauskas et al., “Dynamic modes of the flipped-out cytosine during Hhal methyltransferase-DNA interactions in solution,” The EMBO Journal, vol. 17, No. 1, 1998, pp. 317-324.
Labahn et al., “Three-dimensional structure of the adenine-specific DNA methyltransferase M-Tag I in complex with the cofactor S-adenosylmethionine,” Proc. Natl. Acad. Sci. USA, vol. 91, Nov. 1994, pp. 10957-10961.
Kwoh et al., “Transcription-based amplification system and detection of amplified human immunodeficiency virus type 1 with a bead-based sandwich hybridization format,” Proc. Natl. Acad. Sci. USA, Feb. 1989, vol. 86, pp. 1173-1177.
Kohler et al., “Continuous cultures of fused cells secreting antibody of predefined specificity,” Nature (1975) vol. 256, pp. 495-497.
Ho et al., “Site-directed mutagenesis by overlap extension using the polymerase chain reaction,” Gene 77, (1989) pp. 51-59.
Holz et al., “2-Aminopurine as a fluorescent probe for DNA base flipping by methyltransfeerases,” Nucleic Acids Res. 26, (1998) pp. 1076-1083.
Goedecke et al., “Structure of the N6-adenine DNA methyltransferase M-Tagl in complex with DNA and a cofactor analog,” Nature Struct. Biol. 8, (2001) pp. 121-125.
Koudan et al., “Homology Modelling of the CG-specific DNA Methyltransferase Sssl and its Complexes with DNA and AdoHcy,” J. Biomol Struct. Dyn. 22, (2004) pp. 339-346.
Thomson et al., “Efficient Route to the Pineal Hormone Melatonin by Radical-Based Indole Synthesis,” Synth. Commun. 33, (2003) pp. 3631-3641.
Sambrook et al., “Rapid and Efficient Site-directed Mutagenesis by the Single-tube Megaprimer PCR Method,”(2001) Cold Spring Harbor Laboratory Press, pp. 13.31-13.35.
Jeltsch A, “Beyond Watson and Crick: DNA Methylation and Molecular Enzymology of DNA Methyltransferases,” ChemBioChem 3, (2002) pp. 275-

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