Title:
STABLE ISOTOPE-LABELED AMINO ACID, METHOD OF INTEGRATING THE SAME INTO TARGET PROTEIN, METHOD OF NMR STRUCTURAL ANALYSIS OF PROTEIN AND PROCESS FOR PRODUCING SITE-SELECTIVE STABLE ISOTOPE-LABELED FUMARIC ACID AND TARTARIC ACID
Document Type and Number:
WIPO Patent Application WO/2003/053910
Kind Code:
A1
Abstract:
It is intended to provide a stable isotope-labeled amino acid which is at least one of amino acids constituting protein, characterized by having at least one of the following labeling patterns: (a) in one or more methylene groups, methylene hydrogen atoms other than at least one have been deuterated; (b) in prochiral gem-methyl groups, hydrogen atoms in one of the methyl groups have been completely deuterated; (c) in prochiral gem-methyl groups, hydrogen atoms in the methyl groups have been partially deuterated; and (d) hydrogen atoms in a methyl group other than one have been deuterated while hydrogen atoms in an aromatic ring have been partially deuterated. Using this stable isotope-labeled amino acid, deuterium substitution of a protein can be achieved without worsening the NMR sensitivity of the residual hydrogen nucleus. Thus, an NMR spectrum of a high-molecular weight protein exceeding the upper limit applicable in the prior art can be quickly and surely analyzed and the stereostructure can be highly precisely determined at the same time.
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Inventors:
KAINOSHO MASATSUNE (JP)
TERAUCHI TSUTOMU (JP)
TERAUCHI TSUTOMU (JP)
Application Number:
PCT/JP2002/013303
Publication Date:
July 03, 2003
Filing Date:
December 19, 2002
Export Citation:
Assignee:
JAPAN SCIENCE & TECH CORP (JP)
KAINOSHO MASATSUNE (JP)
TERAUCHI TSUTOMU (JP)
KAINOSHO MASATSUNE (JP)
TERAUCHI TSUTOMU (JP)
International Classes:
C07B59/00; C07C51/09; C07C229/08; C07C229/22; C07C229/24; C07C229/26; C07C229/36; C07C323/58; G01N24/08; (IPC1-7): C07C229/08; C07C229/24; C07C229/26; C07C229/36; C07C323/58; C07B59/00; C12P21/00; G01N24/08
Foreign References:
| JPH02208579A | 1990-08-20 | |||
| JPH05236986A | 1993-09-17 | |||
| EP0299425A1 | 1989-01-18 |
Other References:
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MAHON MARRITA M. ET AL.: "The pyridoxal-5'-phosphate-dependent catalytic antibody 15A9", FEBS LETTERS, vol. 427, no. 1, 1998, pages 74 - 78, XP004259033
MOLDES MILAGROS ET AL.: "Hydrogen-deuterium enchange in the perfused rat liver metabolizing (3-13C) alanine and 2H20 as detected by multinuclear NMR spectroscopy", NMR IN BIOMEDICINE, vol. 7, no. 6, 1994, pages 249 - 262, XP002967615
OBA MAKOTO ET AL.: "Synthesis of 13C/D doubly labeled L-leucines", JOURNAL OF ORGANIC CHEMISTRY, vol. 66, no. 17, 24 August 2001 (2001-08-24), pages 5919 - 5922, XP002967616
SON JONG-KEUN ET AL.: "Stereochemical mechanism of iodoacetic acid mediated decomposition of L-methionine to L-homoserine lactone", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 4, 1989, pages 1363 - 1367, XP002967617
OBA MAKOTO ET AL.: "Synthesis of (3,4-d2)lysine using deuterated pyroglutamate derivative as a chiral template", JAPANESE JOURNAL OF DEUTERIUM SCIENCE, vol. 8, no. 1, 1999, pages 11 - 15, XP002967618
PRABHAKARAN P.C. ET AL.: "Biosynthesis of blasticidin S from L-alpha-arginine", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 110, no. 17, 1988, pages 5785 - 5791, XP002967619
OBA MAKOTO ET AL.: "Synthesis of L-threo- and L-erythro-(1-13C,2,3-2H2)amino acids", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, no. 12, 1995, pages 1603 - 1609, XP002967620
GANI DAVID ET AL.: "Synthesis of a monocyclic beta-lactam stereospecifically labeled at C-4", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY (1972-1999), no. 11, 1983, pages 2811 - 2814, XP002967621
OBA MAKOTO ET AL.: "Stereoselective synthesis of deuterium-labeled amino acids using diketopipiperazine or proline derivatives as a chiral template", JURNAL OF DEUTERIUM SCIENCE, vol. 5, no. 1, 1996, pages 35 - 39, XP002967622
EASTON CHRISTOPHER ET AL.: "Synthesis of each stereoisomer of (3-2H1)phenylalanine and evaluation of the stereochemical course of the reaction of (R)-phenylalanine with (S)-phenylalamine ammonia-lyase", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, no. 24, 1994, pages 3545 - 3548, XP002967623
MOCEK URSULA ET AL.: "Biosynthesis of the modified peptide antibiotic thiostrepton in streptomyces szureus and streptomyces laurentii", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 115, no. 18, 1993, pages 7992 - 8001, XP002967624
KOBAYASHI J. ET AL.: "Nuclear magnetic resonance study of side-chain conformation of tyrosyl residue in (Met5)-enkephalin", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 621, no. 2, 1980, pages 190 - 203, XP002967625
OBA MAKOTO ET AL.: "Asymmetric synthesis of L-proline regio- and stereoselectively labeled with deuterium", TETRAHEDRON: ASYMMETRY, vol. 10, no. 5, 1999, pages 937 - 945, XP004162517
TSUTOMU HOSHINO ET AL.: "Studies on the biosynthesis of violacein. Part II", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 51, no. 10, 1987, pages 2733 - 2741, XP002967626
THE JAPANESE BIOCHEMICAL SOCIETY, 1991, TOKYO KAGAKU DOJIN, article "Shinsei kagaku jikken koza 1 tanpakushitsu IV", pages: 204 - 206, XP002967627, 1
E. KARIYA ET AL., J. BIOMOL. NMR, vol. 18, 2000, pages 75 - 76
MAKOTO OBA ET AL., J. CHEM. SOC., PERKIN TRANS., vol. 1, 1995, pages 1603
E. KARIA ET AL., J. BIOMOL. NMR, vol. 18, 2000, pages 75 - 76
MAHON MARRITA M. ET AL.: "The pyridoxal-5'-phosphate-dependent catalytic antibody 15A9", FEBS LETTERS, vol. 427, no. 1, 1998, pages 74 - 78, XP004259033
MOLDES MILAGROS ET AL.: "Hydrogen-deuterium enchange in the perfused rat liver metabolizing (3-13C) alanine and 2H20 as detected by multinuclear NMR spectroscopy", NMR IN BIOMEDICINE, vol. 7, no. 6, 1994, pages 249 - 262, XP002967615
OBA MAKOTO ET AL.: "Synthesis of 13C/D doubly labeled L-leucines", JOURNAL OF ORGANIC CHEMISTRY, vol. 66, no. 17, 24 August 2001 (2001-08-24), pages 5919 - 5922, XP002967616
SON JONG-KEUN ET AL.: "Stereochemical mechanism of iodoacetic acid mediated decomposition of L-methionine to L-homoserine lactone", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 4, 1989, pages 1363 - 1367, XP002967617
OBA MAKOTO ET AL.: "Synthesis of (3,4-d2)lysine using deuterated pyroglutamate derivative as a chiral template", JAPANESE JOURNAL OF DEUTERIUM SCIENCE, vol. 8, no. 1, 1999, pages 11 - 15, XP002967618
PRABHAKARAN P.C. ET AL.: "Biosynthesis of blasticidin S from L-alpha-arginine", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 110, no. 17, 1988, pages 5785 - 5791, XP002967619
OBA MAKOTO ET AL.: "Synthesis of L-threo- and L-erythro-(1-13C,2,3-2H2)amino acids", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, no. 12, 1995, pages 1603 - 1609, XP002967620
GANI DAVID ET AL.: "Synthesis of a monocyclic beta-lactam stereospecifically labeled at C-4", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY (1972-1999), no. 11, 1983, pages 2811 - 2814, XP002967621
OBA MAKOTO ET AL.: "Stereoselective synthesis of deuterium-labeled amino acids using diketopipiperazine or proline derivatives as a chiral template", JURNAL OF DEUTERIUM SCIENCE, vol. 5, no. 1, 1996, pages 35 - 39, XP002967622
EASTON CHRISTOPHER ET AL.: "Synthesis of each stereoisomer of (3-2H1)phenylalanine and evaluation of the stereochemical course of the reaction of (R)-phenylalanine with (S)-phenylalamine ammonia-lyase", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, no. 24, 1994, pages 3545 - 3548, XP002967623
MOCEK URSULA ET AL.: "Biosynthesis of the modified peptide antibiotic thiostrepton in streptomyces szureus and streptomyces laurentii", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 115, no. 18, 1993, pages 7992 - 8001, XP002967624
KOBAYASHI J. ET AL.: "Nuclear magnetic resonance study of side-chain conformation of tyrosyl residue in (Met5)-enkephalin", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 621, no. 2, 1980, pages 190 - 203, XP002967625
OBA MAKOTO ET AL.: "Asymmetric synthesis of L-proline regio- and stereoselectively labeled with deuterium", TETRAHEDRON: ASYMMETRY, vol. 10, no. 5, 1999, pages 937 - 945, XP004162517
TSUTOMU HOSHINO ET AL.: "Studies on the biosynthesis of violacein. Part II", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 51, no. 10, 1987, pages 2733 - 2741, XP002967626
THE JAPANESE BIOCHEMICAL SOCIETY, 1991, TOKYO KAGAKU DOJIN, article "Shinsei kagaku jikken koza 1 tanpakushitsu IV", pages: 204 - 206, XP002967627, 1
E. KARIYA ET AL., J. BIOMOL. NMR, vol. 18, 2000, pages 75 - 76
MAKOTO OBA ET AL., J. CHEM. SOC., PERKIN TRANS., vol. 1, 1995, pages 1603
E. KARIA ET AL., J. BIOMOL. NMR, vol. 18, 2000, pages 75 - 76
Attorney, Agent or Firm:
Kumakura, Yoshio (Shin-Tokyo Bldg. 3-1, Marunouchi 3-Chom, Chiyoda-Ku Tokyo, JP)
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