Accelerants for the modification of non-natural amino acids...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S081000, C564S148000, C564S226000, C564S235000, C564S310000, C560S159000

Reexamination Certificate

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08071809

ABSTRACT:
Disclosed herein are accelerants for the formation of oxime-containing compounds from the reaction of a carbonyl-containing compound and a hydroxylamine-containing compound. The oxime-containing compound, the carbonyl-containing compound and the hydroxylamine-containing compound can each be a non-natural amino acid or a non-natural amino acid polypeptide. Also disclosed is the use of such accelerants to form oxime-containing compounds, the resulting oxime-containing compounds, and reaction mixtures containing such accelerants.

REFERENCES:
patent: 3859273 (1975-01-01), Beregi et al.
patent: 4680311 (1987-07-01), Watanabe et al.
patent: 5364840 (1994-11-01), Basava et al.
patent: 5484771 (1996-01-01), Beaulieu et al.
patent: 6337191 (2002-01-01), Swartz
patent: 6344483 (2002-02-01), Hallinan et al.
patent: 6448281 (2002-09-01), Beaulieu
patent: 6449281 (2002-09-01), Smith
patent: 6455550 (2002-09-01), Chen et al.
patent: 6608196 (2003-08-01), Wang
patent: 6900218 (2005-05-01), Wang
patent: 7056942 (2006-06-01), Hildesheim et al.
patent: 7332571 (2008-02-01), Miao et al.
patent: 7385028 (2008-06-01), Miao et al.
patent: 7468458 (2008-12-01), Tian et al.
patent: 7638491 (2009-12-01), Miao et al.
patent: 7696312 (2010-04-01), Miao et al.
patent: 7888533 (2011-02-01), Tian et al.
patent: 2002/0065418 (2002-05-01), Beaulieu
patent: 2002/0081660 (2002-06-01), Swartz
patent: 2003/0072746 (2003-04-01), Miller
patent: 2006/0217289 (2006-09-01), Miao et al.
patent: 2008/0118464 (2008-05-01), Miao et al.
patent: 2008/0139793 (2008-06-01), Tian et al.
patent: 2008/0153979 (2008-06-01), Miao et al.
patent: 2008/0154058 (2008-06-01), Tian et al.
patent: 2008/0177027 (2008-07-01), Miao et al.
patent: 2008/0177038 (2008-07-01), Miao et al.
patent: 2008/0182968 (2008-07-01), Miao et al.
patent: 2008/0182969 (2008-07-01), Miao et al.
patent: 2008/0213840 (2008-09-01), Miao et al.
patent: 2008/0268518 (2008-10-01), Miao et al.
patent: 2008/0268519 (2008-10-01), Miao et al.
patent: 2009/0111147 (2009-04-01), Miao et al.
patent: 2009/0123968 (2009-05-01), Miao et al.
patent: 2110543 (1994-06-01), None
patent: 0605963 (1994-07-01), None
patent: WO-90-05785 (1990-05-01), None
patent: WO-96-41813 (1996-12-01), None
patent: WO-1999-52539 (1999-10-01), None
patent: WO-00-055353 (2000-09-01), None
patent: WO-03-044056 (2003-05-01), None
patent: WO-2006-069246 (2006-06-01), None
patent: WO-2006-069246 (2006-06-01), None
patent: WO-2007-056448 (2007-05-01), None
patent: WO-2007-056448 (2007-05-01), None
patent: WO-2007-070659 (2007-06-01), None
patent: WO-2007-070659 (2007-06-01), None
patent: WO-2007-079130 (2007-07-01), None
patent: WO-2007-079130 (2007-07-01), None
Alpha Interferon, GenBank Accession No. AAA37889, pp. 1-2. Accessed Jan. 16, 2009.
Anderson et al., “Exploring the Limits of Codon and Anticodon Size,” Chem. And Biol. 9:237-244 (2002).
Arnold, Z.S. et al., “Optically Active Aromatic Amino Acids. Part VI. Synthesis and Properties of [Leuimg id="CUSTOM-CHARACTER-00001" he="1.44mm" wi="2.79mm" file="US08071809-20111206-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?5]-enkephaline Analogues Containing O-methyl-L-Tyrosineimg id="CUSTOM-CHARACTER-00002" he="1.44mm" wi="2.79mm" file="US08071809-20111206-P00002.TIF" alt="custom character" img-content="character" img-format="tif" ?1 with Ring Substitution at Position 3′,” J. Peptide Sci. 6:280-289 (2000).
Auerbach et al., “Angiogenesis assays: Problems and pitfalls,” Cancer and Metastasis Reviews 19:167-172 (2000).
Bain, J.D. et al., “Biosynthetic site-specific incorporation of a non-natural amino acid into a polypeptide,” J. Am. Chem. Soc. 111:8013-8014 (1989).
Basu et al., “Catalytic transfer reduction of conjugated alkenes and an imine using polymer-supported formates,” Tetrahedron Ltrs. 44:8931-8934 (2003).
Berendsen, H.J.C., “A Glimpse of the Holy Grail?”, Science 282:642-643 (1998).
Beta Interferon, GenBank Accession No. NP—002167, pp. 1-3. Accessed Jan. 16, 2009.
Boles, J.O. et al., Nat. Struct. Biol. 1:5:283-284 (1994).
Bradley et al., “Limits of Cooperativity in a Structurally modular protein: Response of the Notice Ankyrin Domain to Analogous Alanine Substitutions in Each Repeat,” J. Mol. Biol. 324:3;73-386 (2002).
Brannigan et al., “Protein engineering 20 years on,” Nature 3:964-970 (2002).
Brunner, J., “New Photolabeling and crosslinking methods,” Ann. Rev. Biochem. vol. 62, pp. 483-514 (1993).
Buckel, Recombinant Protein Drugs: Milestones in Drug Therapy, Bitkhauser Verlag, eds. 2001, Preface and pp. 191-197.
Budisa, N. et al., Eur. J. Biochem. 230:788-796 (1995).
Budisa, N. et al., FASEB J. 13:41-51 (1999).
Carrasco, M.R. and Brown, R.T., J. Org. Chem. 68:8853-8858 (2003).
Chin, J. et al., “An Expanded Eukaryotic Genetic Code,” Science 301:964-967 (2003).
Chin, J.W. et al., “Addition of a photocrosslinking amino acid to the genetic code ofEscherichia coli,” PNAS USA 99:11020-11024 (2002).
Chin, J.W., et al., “Addition ofp-Azido-L-phenylalanine to the Genetic Code ofEscherichia coli,” JACS 124:9026-9027 (2002).
Chin, J.W. and Schultz, P.G., “In Vivo Photocrosslinking with Unnatural Amino Acid Mutagenesis,” Chem. Bio. Chem. 11:1135-1137 (2002).
Clinical Aspects of Cancer from Merck Manual, pp. 1-4. Accessed 20/20/2008.
Cordes, E. and Jencks, W., “Nucleophilic Catalysis of Semicarbazone Formation by Anilines,” J. Am. Chem. Soc., 1962, 84, pp. 826-831, (1962).
Corey, D.R. And Schult, P.G., “Generation of a hybrid sequence-specific single-stranded deoxyribonuclease,” Science, vol. 238, pp. 1401-1403 (1987).
Crick, F.J.C., et al., “General nature of the genetic code for proteins,” Nature vol. 192, No. 4809, pp. 1227-1232(1961).
Dennis et al., J. Biol. Chem. 277:38:35035-35043 (2002).
Designing Custom Peptides, SIGMA, accessed Dec. 16, 2004.
Doring, V. et al., Science 292:501-504 (2001).
Dougherty, “Unnatural Amino Acids as Probes of Protein Structure and Function,” Curr. Op. Chem. Biol.l 4:645-652 (2000).
Duewel, H. et al., Biochemistry 36:3404-3416 (1997).
Ellman, J.A. et al, “Biosynthetic method for introducing unnatural amino acidssite-specifically into proteins,” Methods in Enz. vol. 202, pp. 301-336 (1992).
Ellman, J.A. et al, “Site-specific incorporation of novel backbone structures into proteins,” Science vol. 255, pp. 197-200 (1992).
England, P.M. et al., Cell 96:89-98 (1999).
Forster, A. et al., PNAS USA 100:11:6353-6357 (2003).
Frankel, A. et al., Chem. & Biol. 10:1043-1050 (2003).
Furter, R., Protein Sci. 7:419-426 (1998).
Gallivan, J.P. et al., Chem. Biol. 4:10:739-749 (1997).
Gao, Y., “Inhibition of Grb2 SH2 Domain Binding by Non-Phosphate-Containing Ligands. 2.4-(20Malonyl)phenylalanine as a Potent Phosphotyrosyl Mimetic,” J. Med. Chem. 43:911.-920 (2000).
Geoghegan, K. and Stroh, J., Bioconjug. Chem. 3:138-146 (1992).
Guckian and Kool, Angew. Chem. Int. Ed. Engl. 36:24:2825-2828 (1998).
Gura, “Systems for Identifying New Drugs Are Often Faulty,” Cancer Models, Science 278:1041-1042 (1997).
Hamano-Takaku, F. et al., J. Biol. Chem. 275, No. 51:40324-40328 (2000).
Hang, H. and Bertozzi, C., Acc. Chem. Res. 34:9:727-736 (2001).
Harris, J.M., “Laboratory Synthesis of Polyethylene Glycol Derivatives,” JMS-Rev. Macromol. Chem. Phys. C25(3):325-373 (1985).
Hartman, G., “A Convenient Synthesis of 4-Aminomethyl-L-Phenylalanine,” Synth. Comm. 21(20):2103-2107 (1991).
Hendrickson, W.A., et al., EMBO J. 9:5:1665-1672 (1990).
Hirao et al., “An unnatural base pair for incorporating amino acid analogues into protein,” Nature Biotech. 20:177-182 (2002).
Hofmann, K. and Bohn, H., “Studies on polypeptides. XXXVI. The effect of pyrazole-imidazole replacements on the S-protein activating potency of an S-peptide fragment,” J. Am. Chem., vol. 88, No. 24, pp.

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