메뉴 건너뛰기




Volumn 45, Issue 48, 2006, Pages 14513-14522

(±)-(1S,2R,5S)-5-amino-2-fluorocyclohex-3-enecarboxylic acid. A potent GABA aminotransferase inactivator that irreversibly inhibits via an elimination-aromatization pathway

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIZATION; CARBOXYLIC ACIDS; CONFORMATIONS; ENZYMES; NEUROLOGY; SUBSTRATES; TRANSCEIVERS;

EID: 33845267173     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi061592m     Document Type: Article
Times cited : (14)

References (42)
  • 1
    • 0016192636 scopus 로고
    • Chemical nature of synaptic transmission in vertebrates
    • Krnjevic, K. (1974) Chemical nature of synaptic transmission in vertebrates, Physiol. Rev. 54, 418-540.
    • (1974) Physiol. Rev. , vol.54 , pp. 418-540
    • Krnjevic, K.1
  • 2
    • 0024459858 scopus 로고
    • GABA in epilepsy: The pharmacologic basis
    • Gale, K. (1989) GABA in epilepsy: The pharmacologic basis, Epilepsia 30 (Suppl. 3), S1-S11.
    • (1989) Epilepsia , vol.30 , Issue.SUPPL. 3
    • Gale, K.1
  • 3
    • 0001943869 scopus 로고
    • (Roberts, E., Chase, T. N., and Tower, D. B., Eds.) Raven Press, New York
    • Hornykiewicz, O., Lloyd, K. B., and Davidson, L. (1976) in GABA in nervous system function (Roberts, E., Chase, T. N., and Tower, D. B., Eds.) pp 479-485, Raven Press, New York.
    • (1976) GABA in Nervous System Function , pp. 479-485
    • Hornykiewicz, O.1    Lloyd, K.B.2    Davidson, L.3
  • 4
    • 13644253001 scopus 로고
    • Amino acids in plasma, cerebrospinal fluid, and brain of patients with Huntington's chorea
    • Perry, T. L., Hansen, S., Lesk, D., and Kloster, M. (1972) Amino acids in plasma, cerebrospinal fluid, and brain of patients with Huntington's chorea, Adv. Neurol. 1, 609-618.
    • (1972) Adv. Neurol. , vol.1 , pp. 609-618
    • Perry, T.L.1    Hansen, S.2    Lesk, D.3    Kloster, M.4
  • 5
    • 0028954665 scopus 로고
    • Basic aspects of GABA-transaminase in neuropsychiatric disorders
    • Sherif, F. M., and Ahmed, S. S. (1995) Basic aspects of GABA-transaminase in neuropsychiatric disorders, Clin. Biochem. 28, 145-154.
    • (1995) Clin. Biochem. , vol.28 , pp. 145-154
    • Sherif, F.M.1    Ahmed, S.S.2
  • 6
    • 0017331197 scopus 로고
    • 4-Amino-hex-5-enoic acid, a selective catalytic inhibitor of 4-aminobutyric acid aminotransferase in mammalian brain
    • (a) Lippert, B., Metcalf, B. W., Jung, M. J., and Casara, P. (1977) 4-Amino-hex-5-enoic acid, a selective catalytic inhibitor of 4-aminobutyric acid aminotransferase in mammalian brain, Eur. J. Biochem. 74, 441-445.
    • (1977) Eur. J. Biochem. , vol.74 , pp. 441-445
    • Lippert, B.1    Metcalf, B.W.2    Jung, M.J.3    Casara, P.4
  • 7
    • 0021342744 scopus 로고
    • Double-blind study of γ-vinyl GABA in patients with refractory epilepsy
    • (b) Rimmer, E. M., and Richens, A. (1984) Double-blind study of γ-vinyl GABA in patients with refractory epilepsy, Lancet 1, 189-190.
    • (1984) Lancet , vol.1 , pp. 189-190
    • Rimmer, E.M.1    Richens, A.2
  • 8
    • 0022873445 scopus 로고
    • Vigabatrin in the treatment of epilepsy: A double-blind, placebo-controlled study
    • (c) Tartara, A., Manni, R., Galimerti, C. A., Hardenberg, J., Orwin, J., and Perrucca, E. (1986) Vigabatrin in the treatment of epilepsy: A double-blind, placebo-controlled study, Epilepsia 27, 717-723.
    • (1986) Epilepsia , vol.27 , pp. 717-723
    • Tartara, A.1    Manni, R.2    Galimerti, C.A.3    Hardenberg, J.4    Orwin, J.5    Perrucca, E.6
  • 11
    • 32844472472 scopus 로고    scopus 로고
    • Syntheses and evaluation of fluorinated conformationally restricted analogues of GABA as potential inhibitors of GABA aminotransferase
    • Wang, Z., and Silverman, R. B. (2006) Syntheses and evaluation of fluorinated conformationally restricted analogues of GABA as potential inhibitors of GABA aminotransferase, Bioorg. Med. Chem. 14, 2242-2252.
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 2242-2252
    • Wang, Z.1    Silverman, R.B.2
  • 12
    • 0034001395 scopus 로고    scopus 로고
    • A new class of conformationally rigid analogs of 4-amino-5-halopentanoic acids, potent inactivators of γ-aminobutyric acid aminotransferase
    • Qiu, J., and Silverman, R. B. (2000) A new class of conformationally rigid analogs of 4-amino-5-halopentanoic acids, potent inactivators of γ-aminobutyric acid aminotransferase, J. Med. Chem. 43, 706-720.
    • (2000) J. Med. Chem. , vol.43 , pp. 706-720
    • Qiu, J.1    Silverman, R.B.2
  • 13
    • 8344248823 scopus 로고    scopus 로고
    • Mechanistic crystallography. Mechanism of inactivation of γ-aminobutyric acid aminotransferase by (1R,3S,4S)-3-amino-4- fluorocyclopentane-1-carboxylic acid as elucidated by crystallography
    • Storici, P., Qiu, J., Schirmer, T., and Silverman, R. B. (2004) Mechanistic crystallography. Mechanism of inactivation of γ-aminobutyric acid aminotransferase by (1R,3S,4S)-3-amino-4-fluorocyclopentane-1-carboxylic acid as elucidated by crystallography, Biochemistry 43, 14057-14063.
    • (2004) Biochemistry , vol.43 , pp. 14057-14063
    • Storici, P.1    Qiu, J.2    Schirmer, T.3    Silverman, R.B.4
  • 14
    • 0033523938 scopus 로고    scopus 로고
    • Inhibition and substrate activity of conformationally-rigid vigabatrin analogues with γ-aminobutyric acid aminotransferase
    • Qiu, J., Pingsterhaus, J. M., and Silverman, R. B. (1999) Inhibition and substrate activity of conformationally-rigid vigabatrin analogues with γ-aminobutyric acid aminotransferase, J. Med. Chem. 42, 4725-4728.
    • (1999) J. Med. Chem. , vol.42 , pp. 4725-4728
    • Qiu, J.1    Pingsterhaus, J.M.2    Silverman, R.B.3
  • 15
    • 0037181037 scopus 로고    scopus 로고
    • Design of a conformationally-restricted analogue of the antiepilepsy drug vigabatrin that directs its mechanism of inactivation of γ-aminobutyric acid aminotransferase
    • Choi, S., Storici, P., Schirmer, T., and Silverman, R. B. (2002) Design of a conformationally-restricted analogue of the antiepilepsy drug vigabatrin that directs its mechanism of inactivation of γ-aminobutyric acid aminotransferase, J. Am. Chem. Soc. 124, 1620-1624.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1620-1624
    • Choi, S.1    Storici, P.2    Schirmer, T.3    Silverman, R.B.4
  • 16
    • 0017653132 scopus 로고
    • Mechanism of the irreversible inhibition of γ-aminobutyric acid-α-ketoglutaric acid transaminase by the neurotoxin gabaculine
    • (a) Rando, R. R. (1977) Mechanism of the irreversible inhibition of γ-aminobutyric acid-α-ketoglutaric acid transaminase by the neurotoxin gabaculine, Biochemistry 16, 4604-4610.
    • (1977) Biochemistry , vol.16 , pp. 4604-4610
    • Rando, R.R.1
  • 17
    • 0032802059 scopus 로고    scopus 로고
    • Isolation and characterization of the product of inactivation of γ-aminobutyric acid aminotransferase by gabaculine
    • (b) Fu, M., and Silverman, R. B. (1999) Isolation and characterization of the product of inactivation of γ-aminobutyric acid aminotransferase by gabaculine, Bioorg. Med. Chem. 7, 1581-1590.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 1581-1590
    • Fu, M.1    Silverman, R.B.2
  • 18
    • 0018699667 scopus 로고
    • Molecular basis for the irreversible inhibition of 4-aminobutyric acid:2-oxoglutarate and L-ornithine:2-oxoacid aminotransferases by 3-amino-1,5-cyclohexadienyl carboxylic acid (isogabaculine)
    • Metcalf, B. W., and Jung, M. J. (1979) Molecular basis for the irreversible inhibition of 4-aminobutyric acid:2-oxoglutarate and L-ornithine:2-oxoacid aminotransferases by 3-amino-1,5-cyclohexadienyl carboxylic acid (isogabaculine), Mol. Pharmacol. 16, 539-545.
    • (1979) Mol. Pharmacol. , vol.16 , pp. 539-545
    • Metcalf, B.W.1    Jung, M.J.2
  • 19
    • 0032542755 scopus 로고    scopus 로고
    • An aromatization mechanism of inactivation of γ-aminobutyric acid aminotransferase for the antibiotic L-cycloserine
    • Olson, G. T., Fu, M., Lau, S., Rinehart, K. L., and Silverman, R. B. (1998) An aromatization mechanism of inactivation of γ-aminobutyric acid aminotransferase for the antibiotic L-cycloserine, J. Am. Chem. Soc. 120, 2256-2267.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2256-2267
    • Olson, G.T.1    Fu, M.2    Lau, S.3    Rinehart, K.L.4    Silverman, R.B.5
  • 20
    • 0021829938 scopus 로고
    • 4-Amino-4,5-dihydrothiophene-2-carboxylic acid
    • Adams, J. L., Chen, T. M., and Metcalf, B. W. (1985) 4-Amino-4,5- dihydrothiophene-2-carboxylic acid, J. Org. Chem. 50, 2730-2736.
    • (1985) J. Org. Chem. , vol.50 , pp. 2730-2736
    • Adams, J.L.1    Chen, T.M.2    Metcalf, B.W.3
  • 21
    • 0021157901 scopus 로고
    • Enantiospecific synthesis of (S)-4-amino-4,5-dihydro-2-furancarboxylic acid, a new suicide inhibitor of GABA-transaminase
    • Burkhart, J. P., Holbert, G. W., and Metcalf, B. W. (1984) Enantiospecific synthesis of (S)-4-amino-4,5-dihydro-2-furancarboxylic acid, a new suicide inhibitor of GABA-transaminase, Tetrahedron Lett. 25, 5267-5270.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5267-5270
    • Burkhart, J.P.1    Holbert, G.W.2    Metcalf, B.W.3
  • 22
    • 0033198649 scopus 로고    scopus 로고
    • Mechanism of inactivation of γ-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-thiophenecarboxylic acid
    • Fu, M., Nikolic, D., Van Breemen, R., and Silverman, R. B. (1999) Mechanism of inactivation of γ-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-thiophenecarboxylic acid, J. Am. Chem. Soc. 121, 7751-7759.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7751-7759
    • Fu, M.1    Nikolic, D.2    Van Breemen, R.3    Silverman, R.B.4
  • 23
    • 0346887166 scopus 로고    scopus 로고
    • Inactivation of γ-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-furancar boxylic acid does not proceed by the expected aromatization mechanism
    • Fu, M., and Silverman, R. B. (2004) Inactivation of γ-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-furancar boxylic acid does not proceed by the expected aromatization mechanism, Bioorg. Med. Chem. Lett. 14, 203-206.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 203-206
    • Fu, M.1    Silverman, R.B.2
  • 25
    • 0010636734 scopus 로고
    • A stereospecific synthesis of D-(-)-shikimic acid
    • Smissman, E. E., Suh, J. T., Oxman, M., and Daniels, R. (1962) A stereospecific synthesis of D-(-)-shikimic acid, J. Am. Chem. Soc. 84, 1040-1041.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 1040-1041
    • Smissman, E.E.1    Suh, J.T.2    Oxman, M.3    Daniels, R.4
  • 27
    • 0019876595 scopus 로고
    • 4-Aminobutyrate aminotransferase. The presence of nonequivalent binding sites
    • Churchich, J. E., and Moses, U. (1981) 4-Aminobutyrate aminotransferase. The presence of nonequivalent binding sites, J. Biol. Chem. 256, 1101-1104.
    • (1981) J. Biol. Chem. , vol.256 , pp. 1101-1104
    • Churchich, J.E.1    Moses, U.2
  • 28
    • 45549111632 scopus 로고
    • An improved assay for 4-aminobutyrate:2-oxoglutarate aminotransferase
    • Jeffery, D., Weitzman, P. D. J., and Lunt, G. G. (1988) An improved assay for 4-aminobutyrate:2-oxoglutarate aminotransferase, Insect Biochem. 28, 347-349.
    • (1988) Insect Biochem. , vol.28 , pp. 347-349
    • Jeffery, D.1    Weitzman, P.D.J.2    Lunt, G.G.3
  • 29
    • 84965093141 scopus 로고
    • Soluble γ-aminobutyric-glutamic transaminase from Pseudomonas fluorescens
    • Scott, E. M., and Jakoby, W. B. (1981) Soluble γ-aminobutyric- glutamic transaminase from Pseudomonas fluorescens, J. Biol. Chem. 234, 932-936.
    • (1981) J. Biol. Chem. , vol.234 , pp. 932-936
    • Scott, E.M.1    Jakoby, W.B.2
  • 30
    • 73649151319 scopus 로고
    • Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase
    • Kitz, R., and Wilson, I. B. (1962) Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase, J. Biol. Chem. 237, 3245-3249.
    • (1962) J. Biol. Chem. , vol.237 , pp. 3245-3249
    • Kitz, R.1    Wilson, I.B.2
  • 31
    • 5244232857 scopus 로고
    • A direct method for the construction of benzene rings, and its use in the total synthesis of ismine
    • Hill, R. K., and Carlson, R. M. (1964) A direct method for the construction of benzene rings, and its use in the total synthesis of ismine, Tetrahedron Lett., 1157-1160.
    • (1964) Tetrahedron Lett. , pp. 1157-1160
    • Hill, R.K.1    Carlson, R.M.2
  • 32
    • 85077634689 scopus 로고
    • The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products
    • (a) Mitsunobu, O. (1981) The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products, Synthesis, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 33
    • 0025907660 scopus 로고
    • Efficacious modification of the Mitsunobu reaction for inversions of sterically hindered secondary alcohols
    • (b) Martin, S. F., and Dodge, J. A. (1991) Efficacious modification of the Mitsunobu reaction for inversions of sterically hindered secondary alcohols, Tetrahedron Lett. 32, 3017-3020.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3017-3020
    • Martin, S.F.1    Dodge, J.A.2
  • 34
    • 0000870705 scopus 로고    scopus 로고
    • The effect of acid strength on the Mitsunobu esterification reaction: Carboxyl vs hydroxyl reactivity
    • (c) Hughes, D. L., and Reamer, R. A. (1996) The effect of acid strength on the Mitsunobu esterification reaction: Carboxyl vs hydroxyl reactivity, J. Org. Chem. 61, 2967-2971.
    • (1996) J. Org. Chem. , vol.61 , pp. 2967-2971
    • Hughes, D.L.1    Reamer, R.A.2
  • 35
    • 33847800447 scopus 로고
    • New fluorinating reagents. Dialkylaminosulfur fluorides
    • Middleton, W. (1975) New fluorinating reagents. Dialkylaminosulfur fluorides, J. Org. Chem. 40, 574-578.
    • (1975) J. Org. Chem. , vol.40 , pp. 574-578
    • Middleton, W.1
  • 36
    • 0035833685 scopus 로고    scopus 로고
    • Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters
    • Gomez-Vidal, J. A., Forrester, M. T., and Silverman, R. B. (2001) Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters, Org. Lett. 3, 2477-2479.
    • (2001) Org. Lett. , vol.3 , pp. 2477-2479
    • Gomez-Vidal, J.A.1    Forrester, M.T.2    Silverman, R.B.3
  • 37
    • 0003686469 scopus 로고
    • Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent
    • Olah, G. A., Narang, S. C., Gupta, B. G. B., and Malhotra, R. (1979) Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/ sodium iodide, a convenient in situ iodotrimethylsilane reagent, J. Org. Chem. 44, 1247-1251.
    • (1979) J. Org. Chem. , vol.44 , pp. 1247-1251
    • Olah, G.A.1    Narang, S.C.2    Gupta, B.G.B.3    Malhotra, R.4
  • 38
    • 0000865359 scopus 로고
    • Steroids. Part XI. Diphenylphosphoryl azide. A novel reagent for the stereospecific synthesis of azides from alcohols
    • Lal, B., Pramanik, B. N., Manhas, M. S., and Bose, A. K. (1977) Steroids. Part XI. Diphenylphosphoryl azide. A novel reagent for the stereospecific synthesis of azides from alcohols, Tetrahedron Lett., 1977-1980.
    • (1977) Tetrahedron Lett. , pp. 1977-1980
    • Lal, B.1    Pramanik, B.N.2    Manhas, M.S.3    Bose, A.K.4
  • 40
    • 0021336190 scopus 로고
    • Synthetic studies on biologically active natural products by a chemicoenzymic approach. Enantioselective synthesis of C- and N-nucleosides, showdomycin, 6-azapseudouridine and cordycepin
    • (b) Ohno, M., Ito, Y., Arita, M., Shibata, T., Adachi, K., and Sawai, H. (1984) Synthetic studies on biologically active natural products by a chemicoenzymic approach. Enantioselective synthesis of C- and N-nucleosides, showdomycin, 6-azapseudouridine and cordycepin, Tetrahedron 40, 145-152.
    • (1984) Tetrahedron , vol.40 , pp. 145-152
    • Ohno, M.1    Ito, Y.2    Arita, M.3    Shibata, T.4    Adachi, K.5    Sawai, H.6
  • 41
    • 0001073140 scopus 로고
    • Reduction of azides by triphenylphosphine in the presence of water: A general and chemoselective access to primary amines
    • Knouzi, N., Vaultier, M., and Carrie, R. (1985) Reduction of azides by triphenylphosphine in the presence of water: A general and chemoselective access to primary amines, Bull. Soc. Chim. Fr., 815-819.
    • (1985) Bull. Soc. Chim. Fr. , pp. 815-819
    • Knouzi, N.1    Vaultier, M.2    Carrie, R.3
  • 42
    • 0026347939 scopus 로고
    • Mechanisms of inactivation of γ-aminobutyric acid aminotransferase by the antiepilepsy drug γ-vinyl GABA (vigabatrin)
    • Nanavati, S. M., and Silverman, R. B. (1991) Mechanisms of inactivation of γ-aminobutyric acid aminotransferase by the antiepilepsy drug γ-vinyl GABA (vigabatrin), J. Am. Chem. Soc. 113, 9341-9349.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9341-9349
    • Nanavati, S.M.1    Silverman, R.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.