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Volumn 49, Issue 22, 2006, Pages 6532-6538

Stereoselective chemoenzymatic synthesis of the four stereoisomers of L-2-(2-carboxycyclobutyl)glycine and pharmacological characterization at human excitatory amino acid transporter subtypes 1, 2, and 3

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 CARBOXYCYCLOBUTYL)GLYCINE; 2 OXALYLCYCLOBUTANECARBOXYLIC ACID DERIVATIVE; ASPARTATE AMINOTRANSFERASE; EXCITATORY AMINO ACID TRANSPORTER; GLYCINE DERIVATIVE; LIGAND; UNCLASSIFIED DRUG;

EID: 33750437268     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060822s     Document Type: Article
Times cited : (28)

References (39)
  • 1
    • 0037286233 scopus 로고    scopus 로고
    • Neuronal high-affinity sodium-dependent glutamate transporters (EAATs): Targets for the development of novel therapeutics against neurodegenerative diseases
    • Campiani, G.; Fattorusso, C.; De Angelis, M.; Catalanotti, B.; Butini, S.; Fattorusso, R.; Fiorini, I.; Nacci, V.; Novellino, E. Neuronal high-affinity sodium-dependent glutamate transporters (EAATs): Targets for the development of novel therapeutics against neurodegenerative diseases. Curr. Pharm. Des. 2003, 9, 599-625.
    • (2003) Curr. Pharm. Des. , vol.9 , pp. 599-625
    • Campiani, G.1    Fattorusso, C.2    De Angelis, M.3    Catalanotti, B.4    Butini, S.5    Fattorusso, R.6    Fiorini, I.7    Nacci, V.8    Novellino, E.9
  • 2
    • 0032925862 scopus 로고    scopus 로고
    • Excitatory amino acid transporters: A family in flux
    • Seal, R. P.; Amara, S. G. Excitatory amino acid transporters: A family in flux. Annu. Rev. Pharm. Toxicol. 1999, 39, 431-456.
    • (1999) Annu. Rev. Pharm. Toxicol. , vol.39 , pp. 431-456
    • Seal, R.P.1    Amara, S.G.2
  • 4
    • 0034065936 scopus 로고    scopus 로고
    • Glutamate as a neurotransmitter in the brain: Review of physiology and pathology
    • Meldrum, B. S. Glutamate as a neurotransmitter in the brain: Review of physiology and pathology. J. Nutr. 2000, 130, 1007S-1015S.
    • (2000) J. Nutr. , vol.130
    • Meldrum, B.S.1
  • 5
    • 29144467608 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3
    • Alaux, S.; Kusk, M.; Sagot, E.; Bolte, J.; Jensen, A. A.; Brauner-Osborne, H.; Gefflaut, T.; Bunch, L. Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3. J. Med. Chem. 2005, 48, 7980-7992.
    • (2005) J. Med. Chem. , vol.48 , pp. 7980-7992
    • Alaux, S.1    Kusk, M.2    Sagot, E.3    Bolte, J.4    Jensen, A.A.5    Brauner-Osborne, H.6    Gefflaut, T.7    Bunch, L.8
  • 6
    • 27844533939 scopus 로고    scopus 로고
    • Azetidinic amino acids: Stereocontrolled synthesis and pharmacological characterization as ligands for glutamate receptors and transporters
    • Bräuner-Osborne, H.; Bunch, L.; Chopin, N.; Couty, F.; Evano, G.; Jensen, A. A.; Kusk, M.; Nielsen, B.; Rabasso, N. Azetidinic amino acids: Stereocontrolled synthesis and pharmacological characterization as ligands for glutamate receptors and transporters. Org. Biomol. Chem. 2005, 3, 3926-3936.
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 3926-3936
    • Bräuner-Osborne, H.1    Bunch, L.2    Chopin, N.3    Couty, F.4    Evano, G.5    Jensen, A.A.6    Kusk, M.7    Nielsen, B.8    Rabasso, N.9
  • 7
    • 30444442997 scopus 로고    scopus 로고
    • Rational design and enantioselective synthesis of (1R,4S,5R,6S)-3- azabicyclo-[3.3.0]octane-4,6-dicarboxylic acid-A novel inhibitor at human glutamate transporter subtypes 1, 2, and 3
    • Bunch, L.; Nielsen, B.; Jensen, A. A.; Brauner-Osborne, H. Rational design and enantioselective synthesis of (1R,4S,5R,6S)-3-azabicyclo-[3.3.0] octane-4,6-dicarboxylic acid-A novel inhibitor at human glutamate transporter subtypes 1, 2, and 3. J. Med. Chem. 2006, 49, 172-178.
    • (2006) J. Med. Chem. , vol.49 , pp. 172-178
    • Bunch, L.1    Nielsen, B.2    Jensen, A.A.3    Brauner-Osborne, H.4
  • 8
    • 0025797354 scopus 로고
    • Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogues
    • Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogues. J. Org. Chem. 1991, 56, 4167-76.
    • (1991) J. Org. Chem. , vol.56 , pp. 4167-4176
    • Shimamoto, K.1    Ishida, M.2    Shinozaki, H.3    Ohfune, Y.4
  • 9
    • 0033607454 scopus 로고    scopus 로고
    • Stereoselective synthesis of L-2-(carboxycyclopropyl)glycines via stereocontrolled 1.3-dipolar cycloadditions of diazomethane on Z- and E-3,4-L-didehydro-glutamates OBO esters
    • Rife, J.; Ortuno, R. M.; Lajoie, G. A. Stereoselective synthesis of L-2-(carboxycyclopropyl)glycines via stereocontrolled 1.3-dipolar cycloadditions of diazomethane on Z- and E-3,4-L-didehydro-glutamates OBO esters. J. Org. Chem. 1999, 64, 8958-8961.
    • (1999) J. Org. Chem. , vol.64 , pp. 8958-8961
    • Rife, J.1    Ortuno, R.M.2    Lajoie, G.A.3
  • 10
    • 0030045674 scopus 로고    scopus 로고
    • Syntheses and conformational analyses of glutamate analogs: 2-(2-Carboxy-3-substituted-cyclopropyl)glycines as useful probes for excitatory amino acid receptors
    • Shimamoto, K.; Ohfune, Y. Syntheses and conformational analyses of glutamate analogs: 2-(2-Carboxy-3-substituted-cyclopropyl)glycines as useful probes for excitatory amino acid receptors. J. Med. Chem. 1996, 39, 407-423.
    • (1996) J. Med. Chem. , vol.39 , pp. 407-423
    • Shimamoto, K.1    Ohfune, Y.2
  • 11
    • 0032485219 scopus 로고    scopus 로고
    • Photocycloaddition of α,β-unsaturated-γ-lactam with ethylene. Synthesis of conformationally restricted glutamate analogues, L-2-(2-carboxycyclobutyl)glycines
    • Tsujishima, H.; Nakatani, K,; Shimamoto, K.; Shigeri, Y.; Yumoto, N.; Ohfune, Y, Photocycloaddition of α,β-unsaturated-γ-lactam with ethylene. Synthesis of conformationally restricted glutamate analogues, L-2-(2-carboxycyclobutyl)glycines. Tetrahedron Lett. 1998, 39, 1193-1196.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1193-1196
    • Tsujishima, H.1    Nakatani, K.2    Shimamoto, K.3    Shigeri, Y.4    Yumoto, N.5    Ohfune, Y.6
  • 12
    • 28644440797 scopus 로고    scopus 로고
    • Synthesis of the constrained glutamate analogues (2S,1′R,2′R) - and (2S,1′s,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination
    • Gu, X.; Xian, M.; Roy-Faure, S.; Bolte, J.; Aitken, D. J.; Gefflaut, T. Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′s,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination. Tetrahedron Lett. 2006, 47, 193-196.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 193-196
    • Gu, X.1    Xian, M.2    Roy-Faure, S.3    Bolte, J.4    Aitken, D.J.5    Gefflaut, T.6
  • 13
    • 0035931557 scopus 로고    scopus 로고
    • Novel biosynthetic routes to nonproteinogenic amino acids as chiral pharmaceutical intermediates
    • Ager, D. J.; Li, T.; Pantaleone, D. P.; Senkpeil, R. F.; Taylor, P. P.; Fotheringham, I. G. Novel biosynthetic routes to nonproteinogenic amino acids as chiral pharmaceutical intermediates. J. Mol. Catal. B 2001, 11, 199-205.
    • (2001) J. Mol. Catal. B , vol.11 , pp. 199-205
    • Ager, D.J.1    Li, T.2    Pantaleone, D.P.3    Senkpeil, R.F.4    Taylor, P.P.5    Fotheringham, I.G.6
  • 14
    • 27944458805 scopus 로고    scopus 로고
    • Revisit of aminotransferase in the genomic era and its application to biocatalysis
    • Hwang, B.-Y.; Cho, B.-K.; Yun, H.; Koteshwar, K.: Kim, B.-G. Revisit of aminotransferase in the genomic era and its application to biocatalysis. J. Mol. Catal. B 2005, 37, 47-55.
    • (2005) J. Mol. Catal. B , vol.37 , pp. 47-55
    • Hwang, B.-Y.1    Cho, B.-K.2    Yun, H.3    Koteshwar, K.4    Kim, B.-G.5
  • 16
    • 0030731779 scopus 로고    scopus 로고
    • Synthesis of optically active amino acids from α-keto acids with Escherichia coli cells expressing heterologous genes
    • Galkin, A.; Kulakova, L.; Yoshimura, T.; Soda, K.; Esaki, N. Synthesis of optically active amino acids from α-keto acids with Escherichia coli cells expressing heterologous genes. Appl. Environ. Microbiol. 1997, 63, 4651-4656.
    • (1997) Appl. Environ. Microbiol. , vol.63 , pp. 4651-4656
    • Galkin, A.1    Kulakova, L.2    Yoshimura, T.3    Soda, K.4    Esaki, N.5
  • 17
    • 8844239142 scopus 로고    scopus 로고
    • Enzymatic resolution for the preparation of enantiomerically enriched D-β-heterocyclic alanine derivatives using Escherichia coli aromatic L-amino acid transaminase
    • Cho, B.-K.; Park, H.-Y.; Seo, J.-H.; Kinnera, K.; Lee, B.-S.; Kim, B.-G. Enzymatic resolution for the preparation of enantiomerically enriched D-β-heterocyclic alanine derivatives using Escherichia coli aromatic L-amino acid transaminase. Biotechnol. Bioeng. 2004, 88, 512-519.
    • (2004) Biotechnol. Bioeng. , vol.88 , pp. 512-519
    • Cho, B.-K.1    Park, H.-Y.2    Seo, J.-H.3    Kinnera, K.4    Lee, B.-S.5    Kim, B.-G.6
  • 18
    • 16344393026 scopus 로고    scopus 로고
    • Asymmetrical synthesis of L-homophenylalanine using engineered escherichia coli aspartate aminotransferase
    • Lo, H.-H.; Hsu, S.-K.; Lin, W.-D.; Chan, N.-L.; Hsu, W.-H. Asymmetrical synthesis of L-homophenylalanine using engineered escherichia coli aspartate aminotransferase. Biotechnol. Prog. 2005, 27, 411-415.
    • (2005) Biotechnol. Prog. , vol.27 , pp. 411-415
    • Lo, H.-H.1    Hsu, S.-K.2    Lin, W.-D.3    Chan, N.-L.4    Hsu, W.-H.5
  • 19
    • 0029782672 scopus 로고    scopus 로고
    • Stereospecific production of the herbicide phosphinothricin (Glufosinate): Purification of aspartate transaminase from Bacillus stearothermophilus, cloning of the corresponding gene, aspC, and application in a coupled transaminase process
    • Bartsch, K.; Schneider, R.; Schulz, A. Stereospecific production of the herbicide phosphinothricin (Glufosinate): Purification of aspartate transaminase from Bacillus stearothermophilus, cloning of the corresponding gene, aspC, and application in a coupled transaminase process. Appl. Environ. Microbiol. 1996, 62, 3794-3799.
    • (1996) Appl. Environ. Microbiol. , vol.62 , pp. 3794-3799
    • Bartsch, K.1    Schneider, R.2    Schulz, A.3
  • 21
    • 4644286944 scopus 로고    scopus 로고
    • Kinetic resolution of (R,S)-secbutylamine using omega-transaminase from Vibrio fluvialis JS17 under reduced pressure
    • Yun, H.; Cho, B.-K.; Kim, B.-G. Kinetic resolution of (R,S)-secbutylamine using omega-transaminase from Vibrio fluvialis JS17 under reduced pressure. Biotechnol. Bioeng. 2004, 87, 772-778.
    • (2004) Biotechnol. Bioeng. , vol.87 , pp. 772-778
    • Yun, H.1    Cho, B.-K.2    Kim, B.-G.3
  • 22
    • 0035433593 scopus 로고    scopus 로고
    • Comparison of the omega-transaminases from different microorganisms and application to production of chiral amines
    • Shin, J. S.; Kim, B. G. Comparison of the omega-transaminases from different microorganisms and application to production of chiral amines. Biosci. Biotechnol. Biochem. 2001, 05, 1782-1788.
    • (2001) Biosci. Biotechnol. Biochem. , vol.5 , pp. 1782-1788
    • Shin, J.S.1    Kim, B.G.2
  • 23
    • 0345393284 scopus 로고    scopus 로고
    • Microbial synthesis of (R)- and (S)-3,4-dimethoxyamphetamines through stereoselective transamination
    • Iwasaki, A.; Yamada, Y.; Ikenaka, Y.; Hasegawa, J. Microbial synthesis of (R)- and (S)-3,4-dimethoxyamphetamines through stereoselective transamination. Biotechnol. Lett. 2003, 25, 1843-1846.
    • (2003) Biotechnol. Lett. , vol.25 , pp. 1843-1846
    • Iwasaki, A.1    Yamada, Y.2    Ikenaka, Y.3    Hasegawa, J.4
  • 24
    • 16544382186 scopus 로고    scopus 로고
    • ω-amino acid:pyruvate transaminase from Alcaligenes denitrificans Y2k-2: A new catalyst for kinetic resolution of b-amino acids and amines
    • Yun, H.; Lim, S.; Cho, B.-K.; Kim, B.-G. ω-amino acid:pyruvate transaminase from Alcaligenes denitrificans Y2k-2: A new catalyst for kinetic resolution of b-amino acids and amines. Appl. Environ. Microbiol. 2004, 70, 2529-2534.
    • (2004) Appl. Environ. Microbiol. , vol.70 , pp. 2529-2534
    • Yun, H.1    Lim, S.2    Cho, B.-K.3    Kim, B.-G.4
  • 25
    • 0035907468 scopus 로고    scopus 로고
    • New probes of the agonist binding site of metabotropic glutamate receptors
    • Bessis, A. S.; Bolte, J.; Pin, J. P.; Acher, F. New probes of the agonist binding site of metabotropic glutamate receptors. Bioorg. Meet Chem. Lett. 2001, 11, 1569-1572.
    • (2001) Bioorg. Meet Chem. Lett. , vol.11 , pp. 1569-1572
    • Bessis, A.S.1    Bolte, J.2    Pin, J.P.3    Acher, F.4
  • 26
    • 0032729656 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of (4S)- and (4R)-4-methyl-2-oxoglutaric acids, precursors of glutamic acid analogues
    • Helaine, V.; Bolte, J. Chemoenzymatic synthesis of (4S)- and (4R)-4-methyl-2-oxoglutaric acids, precursors of glutamic acid analogues. Eur. J. Org. Chem. 1999, 3403, 3-3406.
    • (1999) Eur. J. Org. Chem. , vol.3403 , pp. 3-3406
    • Helaine, V.1    Bolte, J.2
  • 27
    • 0033520212 scopus 로고    scopus 로고
    • A new access to alkyl-alphaketoglutaric acids, precursors of glutamic acid analogues by enzymatic transammation. Application to the synthesis of (2S,4R)-4-propyl-glutamic acid
    • Helaine, V.; Rossi, J.; Bolte, J. A new access to alkyl-alphaketoglutaric acids, precursors of glutamic acid analogues by enzymatic transammation. Application to the synthesis of (2S,4R)-4-propyl-glutamic acid. Tetrahedron Lett. 1999, 40, 6577-6580.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6577-6580
    • Helaine, V.1    Rossi, J.2    Bolte, J.3
  • 28
    • 0141989098 scopus 로고    scopus 로고
    • Synthesis of 4,4-disubstituted L-glutamic acids by enzymatic transamination
    • Helaine, V.; Rossi, J.; Gefflaut, T.; Alaux, S.; Bolte, J. Synthesis of 4,4-disubstituted L-glutamic acids by enzymatic transamination. Adv. Synth. Catal. 2001, 343, 692-697.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 692-697
    • Helaine, V.1    Rossi, J.2    Gefflaut, T.3    Alaux, S.4    Bolte, J.5
  • 29
    • 0347705892 scopus 로고
    • Preparation of the phosphopyridoxamine form of the glutamic-aspartic transaminase
    • Jenkins, W. T.; D'Ari, L. Preparation of the phosphopyridoxamine form of the glutamic-aspartic transaminase. Biochem. Biophys. Res. Commun. 1966, 22, 376-82.
    • (1966) Biochem. Biophys. Res. Commun. , vol.22 , pp. 376-382
    • Jenkins, W.T.1    D'Ari, L.2
  • 30
    • 0000493301 scopus 로고
    • Photochemical [2 + 2] cycloaddition reactions at low temperatures. Synthesis of bridgehead substituted bicyclo [n.2.0]dicarboxylates from maleic acid derivatives and ethylene
    • Bloomfield, J. J.; Owsley, D. C. Photochemical [2 + 2] cycloaddition reactions at low temperatures. Synthesis of bridgehead substituted bicyclo [n.2.0]dicarboxylates from maleic acid derivatives and ethylene. J. Org. Chem. 1971, 36, 3768-73.
    • (1971) J. Org. Chem. , vol.36 , pp. 3768-3773
    • Bloomfield, J.J.1    Owsley, D.C.2
  • 31
    • 33751157335 scopus 로고
    • (Cyanomethylene)phosphoranes as novel carbonyl 1.1-dipole synthons: An efficient synthesis of α-keto acids, esters, and amides
    • Wasserman, H. H.; Ho, W.-B. (Cyanomethylene)phosphoranes as novel carbonyl 1.1-dipole synthons: An efficient synthesis of α-keto acids, esters, and amides. J. Org. Chem. 1994, 59, 4364-6.
    • (1994) J. Org. Chem. , vol.59 , pp. 4364-4366
    • Wasserman, H.H.1    Ho, W.-B.2
  • 32
    • 0024335605 scopus 로고
    • Syntheses of functionalized [beta]-Lactams from tartaric acid
    • Kolasa, T.; J. Miller, M. Syntheses of functionalized [beta]-Lactams from tartaric acid. Tetrahedron 1989, 45, 3071.
    • (1989) Tetrahedron , vol.45 , pp. 3071
    • Kolasa, T.J.1    Miller, M.2
  • 33
    • 2342467905 scopus 로고    scopus 로고
    • Pharmacological characterization of human excitatory amino acid transporters EAAT1, EAAT2 and EAAT3 in a fluorescence-based membrane potential assay
    • Jensen, A. A.; Brauner-Osborne, H. Pharmacological characterization of human excitatory amino acid transporters EAAT1, EAAT2 and EAAT3 in a fluorescence-based membrane potential assay. Biochem. Pharmacol. 2004, 67, 2115-2127.
    • (2004) Biochem. Pharmacol. , vol.67 , pp. 2115-2127
    • Jensen, A.A.1    Brauner-Osborne, H.2
  • 34
    • 0030946093 scopus 로고    scopus 로고
    • Contrasting modes of action of methylglutamate derivatives on the excitatory amino acid transporters, EAAT1 and EAAT2
    • Vandenberg, R. J.; Mitrovic, A. D.; Chebib, M.; Balcar, V. J.; Johnston, G. A. R. Contrasting modes of action of methylglutamate derivatives on the excitatory amino acid transporters, EAAT1 and EAAT2. Mol. Pharmacol. 1997, 51, 809-815.
    • (1997) Mol. Pharmacol. , vol.51 , pp. 809-815
    • Vandenberg, R.J.1    Mitrovic, A.D.2    Chebib, M.3    Balcar, V.J.4    Johnston, G.A.R.5
  • 35
    • 0043085674 scopus 로고
    • A simple method for the preparation of cysteinesulfinic acid
    • Emiliozzi, R.; Pichat, L. A simple method for the preparation of cysteinesulfinic acid. Bull. Soc. Chim. Fr. 1959, 1887-1888.
    • (1959) Bull. Soc. Chim. Fr. , pp. 1887-1888
    • Emiliozzi, R.1    Pichat, L.2
  • 36
    • 0018461805 scopus 로고
    • Crystallization and properties of aspartate-aminotransferase from Escherichia-coli-B
    • Yagi, T.; Kagamiyama, H.; Motosugi, K.; Nozaki, M.; Soda, K. Crystallization and properties of aspartate-aminotransferase from Escherichia-coli-B. FEBS Lett. 1979, 100, 81-84.
    • (1979) FEBS Lett. , vol.100 , pp. 81-84
    • Yagi, T.1    Kagamiyama, H.2    Motosugi, K.3    Nozaki, M.4    Soda, K.5
  • 39
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50% inhibition (150) of an enzymatic reaction
    • Cheng, Y. C.; Prusoff, W. H. Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50% inhibition (150) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
    • (1973) Biochem. Pharmacol. , vol.22 , pp. 3099-3108
    • Cheng, Y.C.1    Prusoff, W.H.2


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