Stable isotope-labeled amino acid and method for...

Drug – bio-affecting and body treating compositions – In vivo diagnosis or in vivo testing – Magnetic imaging agent

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C435S106000, C435S131000, C530S350000

Reexamination Certificate

active

07022310

ABSTRACT:
The present invention provides a stable isotope-labeled amino acid which is at least one of amino acids constituting a protein and which has at least one of the following labeling patterns:(a) hydrogen atoms except at least one hydrogen atom in one or more methylene groups are deuterated,(b) hydrogen atoms in one of prochiral gem-methyl groups are completely deuterated,(c) hydrogen atoms in prochiral methyl groups are partially deuterated, and(d) all hydrogen atoms except one of them in methyl group are deuterated and hydrogen atoms in the aromatic ring are partially deuterated. With the stable isotope-labeled amino acid, the deuteration of protein can be attained without damaging the NMR sensitivity of remaining hydrogen nucleus and, in addition, the rapid, accurate analysis of NMR spectrum of a high-molecular protein which is beyond the limitation in the prior art and the determination of the stereo-structure can be performed at the same time.

REFERENCES:
patent: 0 299 425 (1989-01-01), None
patent: 02208579 (1990-08-01), None
patent: 05236986 (1993-09-01), None
LeMaster, D. 1994. Isotope Labeling in Solution Protein Assignment and Structural Analysis. Progress in NMR Spectroscopy. 26: 400.
Venters, R.A., et al. 1995. High-level 2H/13C/15N labeling of proteins for NMR studies. J. Biomol. NMR 5: 339-344.
Kainosho, M. 1997. Isotope labelling of macromolecules for structural determinations. Nature Structural Biology. NMR suppl. 858-861.
Sattler, M., et al. 1996. Use of deuterium labeling in NMR: overcoming a sizeable problem. Structure. 4:1245-1249.
Y. J. Topper, et al., “Note On The Synthesis Of Succinic Acid Labeled In The Carboxyl Position With Radioactive Carbon”, J. Biol. Chem. 177, 1949, p303-304.
Tohru Oishi, et al., “Highly Enantioselective Dihydroxylation of Trans-Disubstituted and Monosubstituted Olefins”, J. Org. Chem. 1989, 54, pp. 5834-5835.
Stephen Hanessian, et al., “Asymmetric Dihydroxylation of Olefins with a Simple Chiral Ligand”, J. Org. Chem. 1993, 58, pp. 1991-1993.
Kiyoshi Tomioka, et al., “Enantioface Differentiation in Cis Dihydroxylation of C—C Double Bonds by Osmium Tetroxide with Use of a Chiral Diamine with D2Symmetry”, J. Am. Chem. Soc. 1987. 109, pp. 6213-6215.
Masahiro Hirama, et al., “Asymmetric Dihydroxylation of Alkenese with Osmium Tetroxide: Chiral N, N'-Dialkyl-2,2'-bipyrrolidine Complex”, J. Chem. Soc., Chem. Commun., 1989, pp 665-666.
Gianfranco Cainelli, et al., “Catalytic Hydroxylation of Olefins by Polymer-Bound Osmium Tetroxide”, Communications, Jan. 1989, pp. 45-47.
Dario Pini, et al., “Heterogeneous Catalytic Asymmetric Dihydroxylation of Olefins with the OsO4/(9-O-Acylquinine-co-Acrylonitrile) System”, Tetrahedron Letters, vol. 32, No. 38, p. 5175-5178, 1991.
Maritherese Tokles, et al., “Asymmetric Oxidation of Olefins to Vicinal Diols with Osmium Tetroxide”, Tetrahedron Letters, vol. 27, No. 34, pp. 3951-3954, 1986.
Makoto Nakajima, et al., “Highly Enantioselective Dihydroxylation of Olefins by Osmium Tetroxide with Chiral Diamines”, Tetrahedron letters, vol. 49, No. 47, pp. 10973-10806, 1993.
Easton, Christopher J. et al., “Synthesis of Each Stereoisomer of [3-2H1] . . . ” J. Chem. Soc. Perkin Trans. I (1994), pp. 3545-3548.
Erlenmeyer, H. et al., Helv. Chim. Acta, 22, p. 701-706, 1939.
Gani, David et al., Synthesis of a Monocyclic β-Lactam Stereospecifically Labelled at C-4, J. Chem. Soc. Perkin Trans. I 1983, pp. 2811-2814.
Hoshino, Tsutomu et al., “Biosynthesis of Violacein: Origins of Hydrogen, Nitrogen . . . ”, Agric. Biol. Chem., 51 (10), 2733-2741, 1987.
Jorgensen, E.C. et al., “Small Scale Preparation of Carbon-14 Labeled Succinic, Malic, Fumaric and Tartaric Acids”, The Radiation Laboratory and Department of Chemistry, University of California, Berkeley, pp. 2418-2419 (1951).
Kobayashi, J. et al., “Nuclear Magnetic Resonance Study of Side-Chain Conformation of Tyrosyl Residue in [Met5]-Enkephalin”, Biochimica et Biophysica Acta, 621 (1980) 190-203.
Mahon, Marrita, et al., “The pyridoxal-5'-phosphate-dependent catalytic antibody 15A9: its efficiency and stereospecificity in catalyzing the exchange . . . ”, FEBS Letters 427 (1998) 74-78.
Mocek, Ursula et al., “Biosynthesis of the Modified Peptide Antibiotic Thiostrepton inStreptomyces azureusandStreptomyces laurentii”, J. AM. Chem. Soc. 1993, 115, 7992-8001.
Moldes Milagros et al., “1H-2H Exchange in the Perfused Rat Liver Metabolizing . . . ”, NMR IN BIOMEDICINE, vol. 7, 249-262 (1994).
Nystrom, Robert F. et al., J. Am. Chem. Soc., vol. 74, p. 3434, 1952.
Oba, Makoto et al., “Synthesis of 13C/D Doubly Labeled ι-Leucines: Probes for Conformational Analysis of the Leucine Side-chain”, J. Org. Chem. 2001, 66, 5919-5922.
Oba Makoto et al., “Asymmetric synthesis of ι-proline regio- and steroselectively labeled with deuterium”, Tetrahedron Asymmetry 10 (1999) 937-945.
Oba, Makoto et al., “Synthesis of [3,4-D2]Lysine Using Deuterated Pyroglutamate Derivative As A Chiral Template”, Jpn J Deuterium Sci, 1999, 8(1):11-15, p. 11-15.
Oba, Makoto et al., “Stereoselective Synthesis of Deuterium-Labeled Amino Acids Using Diketopiperazine or Proline Derivatives as a Chiral Template”, J Deuterium Sci, (1996), 5(1):35-39.
Oba, Makoto et al., “Synthesis of L-threo- and L-erythro- . . . ”, J. Chem. Soc. Perkin Trans. 1(1995), p. 1603-1609.
Prabhakaran, P.C., “Biosynthesis of Blasticidin S from . . . ”, J. Am. Chem. Soc. (1988), 110, pp. 5785-5791.
Son, Jong-Keun et al., “Stereochemical Mechanism of Iodoacetic Acid Mediated Decomposition of ι-Methionine to ι-Homoserine Lactone”, J. Am. Chem. Soc. (1989), 111, 1363-1367.
Walker, Joel R. et al, “Improved synthesis of (R)-glycine-d-15N”, Tetrahedron 57 (2001) 6695-6701.
Japanese Article (1991), pp. 204-206.
PCT International Search Report.
PCT International Preliminary Examination Report.
PCT Written Opinion.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Stable isotope-labeled amino acid and method for... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Stable isotope-labeled amino acid and method for..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Stable isotope-labeled amino acid and method for... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3527501

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.