aminooxyacetic acid

Summary

Summary: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.

Top Publications

  1. Vedavathi M, Girish K, Kumar M. Isolation and characterization of cytosolic alanine aminotransferase isoforms from starved rat liver. Mol Cell Biochem. 2004;267:13-23 pubmed
    ..Inhibition, modification and spectroscopic studies showed that both PLP and free-SH groups are directly involved in the enzymatic catalysis. PLP activated both the enzymes with a Km 0.057 mM and 0.2 mM for AlaAT I and II respectively...
  2. Hashimoto A, Yoshikawa M. Effect of aminooxyacetic acid on extracellular level of D-serine in rat striatum: an in vivo microdialysis study. Eur J Pharmacol. 2005;525:91-3 pubmed
    To elucidate the effect of an inhibitor of pyridoxal phosphate-dependent enzymes, aminooxyacetic acid, on the activity of serine racemase in vivo, we have investigated the effect of aminooxyacetic acid on the extracellular concentration ..
  3. Zhao W, Ndisang J, Wang R. Modulation of endogenous production of H2S in rat tissues. Can J Physiol Pharmacol. 2003;81:848-53 pubmed
    ..p. injection of PPG. It is concluded that the endogenous production of H2S could be modulated by NO. AOA and PPG have different capacities in regulating the endogenous production of H2S in different types of tissues...
  4. Dever J, Elfarra A. L-methionine-dl-sulfoxide metabolism and toxicity in freshly isolated mouse hepatocytes: gender differences and inhibition with aminooxyacetic acid. Drug Metab Dispos. 2008;36:2252-60 pubmed publisher
    ..Addition of aminooxyacetic acid (AOAA), an inhibitor of transamination reactions, to MetO-exposed male hepatocytes resulted in higher ..
  5. Ishii T, Soeno K, Asami T, Fujioka S, Shimada Y. Arabidopsis seedlings over-accumulated indole-3-acetic acid in response to aminooxyacetic acid. Biosci Biotechnol Biochem. 2010;74:2345-7 pubmed
    Previously we identified aminooxy compounds as auxin biosynthesis inhibitors. One of the compounds, aminooxyacetic acid (AOA) inhibited indole-3-acetic acid (IAA) biosynthesis in rice and tomato...
  6. Yu A, Schousboe A, Hertz L. Metabolic fate of 14C-labeled glutamate in astrocytes in primary cultures. J Neurochem. 1982;39:954-60 pubmed
    ..latter process was unaffected by virtually complete inhibition of glutamate-oxaloacetic transaminase with aminooxyacetic acid, indicating that the formation of alpha-ketoglutarate occurs as an oxidative deamination rather than as a ..
  7. Tominaga K, Yamauchi A, Shuto H, Niizeki M, Makino K, Oishi R, et al. Ovariectomy aggravates convulsions and hippocampal gamma-aminobutyric acid inhibition induced by cyclosporin A in rats. Eur J Pharmacol. 2001;430:243-9 pubmed
    ..A (40 mg/kg, once a day for 5 or 6 days), convulsions and reduction of the basal GABA levels and aminooxyacetic acid-evoked GABA accumulation. These aggravations were blocked by estradiol replacement...
  8. Dirksen A, Dawson P. Rapid oxime and hydrazone ligations with aromatic aldehydes for biomolecular labeling. Bioconjug Chem. 2008;19:2543-8 pubmed publisher
    ..The utility of the approach is demonstrated by the p-fluorobenzylation of human serum albumin and by the fluorescent labeling of an unprotected peptide with Alexa Fluor 488...
  9. Sonnewald U, Kortner T, Qu H, Olstad E, Suñol C, Bak L, et al. Demonstration of extensive GABA synthesis in the small population of GAD positive neurons in cerebellar cultures by the use of pharmacological tools. Neurochem Int. 2006;48:572-8 pubmed
    ..The presence of aminooxyacetic acid (AOAA, 10 microM) which inhibits transaminases and other pyridoxal phosphate dependent enzymes including ..

More Information

Publications62

  1. Ishizaki Koizumi S, Sonaka I, Fujitani S, Nishiguchi S. Mechanisms of the protective effect of L-alanine to D-galactosamine-induced hepatocellular injury: comparative studies of L-alanine and pyruvate. Biochem Biophys Res Commun. 2002;291:738-43 pubmed
    ..These results are consistent with the hypothesis that L-alanine metabolism is important for hepatoprotection, but pyruvate cannot be used as a substitute for L-alanine...
  2. Clark E, Patel S, Chadwick P, Warhurst G, Curry A, Carlson G. Glutamine deprivation facilitates tumour necrosis factor induced bacterial translocation in Caco-2 cells by depletion of enterocyte fuel substrate. Gut. 2003;52:224-30 pubmed
    ..The aim of this study was to investigate the interaction between glutamine metabolism, energy supply, and inflammatory mediators in determining the translocation of non-pathogenic bacteria across cultured enterocytes...
  3. Hatayama T, Takeno K. The metabolic pathway of salicylic acid rather than of chlorogenic acid is involved in the stress-induced flowering of Pharbitis nil. J Plant Physiol. 2003;160:461-7 pubmed
    ..Flowering under long-day conditions induced by low-temperature stress was completely inhibited by aminooxyacetic acid (AOA), an inhibitor of phenylalanine ammonialyase...
  4. Kristiansen S, Løfgren B, Støttrup N, Kimose H, Nielsen Kudsk J, Bøtker H, et al. Cardioprotection by L-glutamate during postischaemic reperfusion: reduced infarct size and enhanced glycogen resynthesis in a rat insulin-free heart model. Clin Exp Pharmacol Physiol. 2008;35:884-8 pubmed publisher
    ..These effects depend on preserved transamination of glutamate and K(ATP) channel activity, but not on insulin administration...
  5. Wu H, Ungerstedt U, Schwarcz R. Regulation of kynurenic acid synthesis studied by microdialysis in the dorsal hippocampus of unanesthetized rats. Eur J Pharmacol. 1992;213:375-80 pubmed
    ..The non-specific inhibitor of kynurenine aminotransferase, aminooxyacetic acid (300 microM), and the depolarizing agent veratridine (50 microM), introduced through the dialysis membrane, ..
  6. Løfgren B, Povlsen J, Rasmussen L, Støttrup N, Solskov L, Krarup P, et al. Amino acid transamination is crucial for ischaemic cardioprotection in normal and preconditioned isolated rat hearts--focus on L-glutamate. Exp Physiol. 2010;95:140-52 pubmed publisher
    ..Underlying mechanisms of IPC include myocardial glutamate metabolism...
  7. Aleo M, Avery M, Beierschmitt W, Drupa C, Fortner J, Kaplan A, et al. The use of explant lens culture to assess cataractogenic potential. Ann N Y Acad Sci. 2000;919:171-87 pubmed
    ..model cataractogen, was attenuated by inhibiting lenticular cysteine conjugate beta-lyase metabolism using aminooxyacetic acid. Finally, this model was used retrospectively to investigate the cataractogenic potential of CJ-12,918 and ..
  8. Rego A, Santos M, Areias F, Proença T, Oliveira C. Glutamate regulates the viability of retinal cells in culture. Vision Res. 2001;41:841-51 pubmed
    ..AOAA (aminooxyacetic acid), a non-specific inhibitor of mitochondrial transaminases, enhanced the intracellular glutamate levels, but ..
  9. Sutch R, Davies C, Bowery N. GABA release and uptake measured in crude synaptosomes from Genetic Absence Epilepsy Rats from Strasbourg (GAERS). Neurochem Int. 1999;34:415-25 pubmed
    ..b>Aminooxyacetic acid (10-100 microM), an inhibitor of GABA-transaminase and, to a lesser extent, glutamate decarboxylase, caused ..
  10. Wakefield S, Lane M, Mitchell M. Impaired mitochondrial function in the preimplantation embryo perturbs fetal and placental development in the mouse. Biol Reprod. 2011;84:572-80 pubmed publisher
    ..These results highlight the importance of mitochondrial function in regulating pre- and postimplantation development; however, the effect on offspring health remains unknown...
  11. Ouaked F, Rozhon W, Lecourieux D, Hirt H. A MAPK pathway mediates ethylene signaling in plants. EMBO J. 2003;22:1282-8 pubmed
    ..In contrast, ctr1 mutants showed constitutive activation of MPK6. These data indicate that a MAPK cascade is part of the ethylene signal transduction pathway in plants...
  12. Koehl J, Djulic A, Kirner V, Nguyen T, Heiser I. Ethylene is required for elicitin-induced oxidative burst but not for cell death induction in tobacco cell suspension cultures. J Plant Physiol. 2007;164:1555-63 pubmed
    ..These results demonstrate evidence for a requirement of the plant hormone ethylene for the onset of the quercinin-induced oxidative burst...
  13. Remiszewska M, Jastrzebski Z, Czyzewska Szafran H, Wutkiewicz M, Czarnecki A. Increased activity of the GABAergic system in selected brain areas after chronic propranolol treatment in spontaneously hypertensive rats. Biochem Pharmacol. 1992;44:465-70 pubmed
    ..Our results indicate that propranolol increases GABAergic system activity. Therefore, we conclude that down-regulation of the GABAergic system in hypertension may be compensated by the regulatory action of propranolol...
  14. Ufnal M, Sikora M, Dudek M. Exogenous hydrogen sulfide produces hemodynamic effects by triggering central neuroregulatory mechanisms. Acta Neurobiol Exp (Wars). 2008;68:382-8 pubmed
    ..The hemodynamic effect seems to be dependent on H2S concentration in cerebrospinal fluid. It appears that the hypertensive response may occur at a concentration, which does not exceed twice the physiological level...
  15. Yamada T, Marubashi W. Overproduced ethylene causes programmed cell death leading to temperature-sensitive lethality in hybrid seedlings from the cross Nicotiana suaveolens x N. tabacum. Planta. 2003;217:690-8 pubmed
    ..Furthermore, the present study has provided the first evidence that ethylene is involved in the phenomenon of hybrid lethality...
  16. Shimizu M, Yamamoto M, Kobayashi M. Effects of a new TRH analogue, YM-14673, on spontaneous motor activity in rats. Arch Int Pharmacodyn Ther. 1989;301:100-11 pubmed
    ..Other possible mechanisms are also discussed...
  17. Carbone S, Ponzo O, Szwarcfarb B, Rondina D, Reynoso R, Scacchi P, et al. Ontogenic modifications in the effect of the GABAergic system on the hypothalamic excitatory amino acids: its relationship with GABAergic control of gonadotrophin secretion during sexual maturation in female rats. Brain Res Dev Brain Res. 2002;133:13-8 pubmed
    b>Aminooxyacetic acid (AOAA), an inhibitor of gamma-aminobutyric transaminase, stimulates the in vitro GABA release by medial and anterior preoptic hypothalamic areas in prepubertal female rats (6, 15 and 30 days of age)...
  18. Foillard S, Rasmussen M, Razkin J, Boturyn D, Dumy P. 1-Ethoxyethylidene, a new group for the stepwise SPPS of aminooxyacetic acid containing peptides. J Org Chem. 2008;73:983-91 pubmed publisher
    ..Since Eei-protected Aoa remains as flexible as normal amino acids in peptide synthesis, it may become the rule for the straightforward preparation of aminooxy peptides...
  19. Bughio N, Nakanishi H, Kiyomiya S, Matsuhashi S, Ishioka N, Watanabe S, et al. Real-time [11C]methionine translocation in barley in relation to mugineic acid phytosiderophore biosynthesis. Planta. 2001;213:708-15 pubmed
    ..Treatment of Fe-deficient plants with aminooxyacetic acid, an inhibitor of nicotianamine aminotransferase, increased the translocation of [11C]methionine to the ..
  20. Yamada T, Marubashi W, Nakamura T, Niwa M. Possible involvement of auxin-induced ethylene in an apoptotic cell death during temperature-sensitive lethality expressed by hybrid between Nicotiana glutinosa and N. repanda. Plant Cell Physiol. 2001;42:923-30 pubmed
    ..Administration of aminooxyacetic acid (AOA) as an ethylene synthesis inhibitor, which could inhibit ethylene production, also showed the same ..
  21. Arun P, Moffett J, Namboodiri A. Evidence for mitochondrial and cytoplasmic N-acetylaspartate synthesis in SH-SY5Y neuroblastoma cells. Neurochem Int. 2009;55:219-25 pubmed publisher
    ..of (14)C-aspartate and (14)C-malate into NAA was examined in the presence and absence of an inhibitor (aminooxyacetic acid, AOAA) of aspartate aminotransferase (AAT), a central enzyme involved in the biosynthesis of aspartate in ..
  22. Lopukhov L, Ponomareva A, Yagodina L. Inhibition of [(15)N]valine transamination during selective labeling of barstar in a T7 polymerase system. Biochemistry (Mosc). 2004;69:806-8 pubmed
    ..We have shown that alpha-aminooxyacetic acid (AOAA) significantly reduces the isotope redistribution, thus increasing the selectivity of (15)N ..
  23. Peng H, Lin T, Wang N, Shih M. Differential expression of genes encoding 1-aminocyclopropane-1-carboxylate synthase in Arabidopsis during hypoxia. Plant Mol Biol. 2005;58:15-25 pubmed
    ..Based on these results, we propose that two signaling pathways are triggered during hypoxia. One pathway leads to the activation of ACS2, ACS6, and ACS7, whereas the other pathway leads to the activation of ADH and ACS9...
  24. Denslow M, Eid T, Du F, Schwarcz R, Lothman E, Steward O. Disruption of inhibition in area CA1 of the hippocampus in a rat model of temporal lobe epilepsy. J Neurophysiol. 2001;86:2231-45 pubmed
    ..in which layer III neurons were selectively destroyed by focal injections of the indirect excitotoxin, aminooxyacetic acid (AOAA)...
  25. Baragatti B, Ciofini E, Sodini D, Luin S, Scebba F, Coceani F. Hydrogen sulfide in the mouse ductus arteriosus: a naturally occurring relaxant with potential EDHF function. Am J Physiol Heart Circ Physiol. 2013;304:H927-34 pubmed publisher
    ..These findings introduce a novel vasoregulatory mechanism into the ductus, with implications for antenatal patency of the vessel and its transitional adjustments at birth...
  26. Johnson E, Lindblom K, Robeson A, Stevens R, Ilkayeva O, Newgard C, et al. Metabolomic profiling reveals a role for caspase-2 in lipoapoptosis. J Biol Chem. 2013;288:14463-75 pubmed publisher
    ..Together, these findings reveal a previously unknown role for caspase-2 as an initiator caspase in lipoapoptosis and suggest that caspase-2 may be an attractive therapeutic target for inhibiting pathological lipid-induced apoptosis...
  27. Mohrenz I, Antonietti P, Pusch S, Capper D, Balss J, Voigt S, et al. Isocitrate dehydrogenase 1 mutant R132H sensitizes glioma cells to BCNU-induced oxidative stress and cell death. Apoptosis. 2013;18:1416-1425 pubmed publisher
    ..and IDH1 KD cells to ROS induction and cell death was further enhanced with the transaminase inhibitor aminooxyacetic acid and under glutamine free conditions, indicating that these cells were more addicted to glutaminolysis...
  28. Cha S, Kim S, Bischoff K, Kim H, Son S, Kang H. Production of a highly group-specific monoclonal antibody against zearalenone and its application in an enzyme-linked immunosorbent assay. J Vet Sci. 2012;13:119-25 pubmed
    ..07 to 123.00% with 0.93 to 2.28% coefficients of variation. Our results demonstrate that the mAb developed in this study could be used to simultaneously screen for ZEN and its metabolites in feed...
  29. Sanders M, Kon C. Glutamine and glutamate metabolism in normal and heat shock conditions in Drosophila Kc cells: conditions supporting glutamine synthesis maximize heat shock polypeptide expression. J Cell Physiol. 1992;150:620-31 pubmed
    ..We conclude that glutamine imposes regulatory changes which alter nitrogen metabolism and support hsp expression in Kc cells...
  30. Baverel G, Martin G, Michoudet C. Glutamine synthesis from aspartate in guinea-pig renal cortex. Biochem J. 1990;268:437-42 pubmed
  31. Medeiros M, Di Mascio P, Gründel S, Soboll S, Sies H, Bechara E. Catabolism of 5-aminolevulinic acid to CO2 by rat liver mitochondria. Arch Biochem Biophys. 1994;310:205-9 pubmed
    ..These data indicate that ALA decarboxylation by the Krebs cycle is a minor process and that it is initiated enzymically (transaminase) and not by metal-catalyzed ALA autoxidation...
  32. Loscher W, Hönack D, Gramer M. Effect of depth electrode implantation with or without subsequent kindling on GABA turnover in various rat brain regions. Epilepsy Res. 1999;37:95-108 pubmed
    ..GABA levels were determined after vehicle injection as well as 30 and 90 min after administration of aminooxyacetic acid (AOAA) at a dose which completely inhibits GABA-T...
  33. El Meskaoui A, Tremblay F. Involvement of ethylene in the maturation of black spruce embryogenic cell lines with different maturation capacities. J Exp Bot. 2001;52:761-9 pubmed
    ..The relationship between ethylene and other phytohormones, and the possible effects of the interaction between ethylene and polyamines on the maturation of the somatic embryos are discussed...
  34. Urbanska E, Chmielewski M, Kocki T, Turski W. Formation of endogenous glutamatergic receptors antagonist kynurenic acid--differences between cortical and spinal cord slices. Brain Res. 2000;878:210-2 pubmed
    Rat spinal cord slices produced kynurenic acid (KYNA) upon exposure to L-kynurenine. Aminooxyacetic acid, non-selective aminotransferase inhibitor, and L-glutamate, but neither N-methyl-D-aspartate (NMDA), alpha-amino-3-hydroxy-5-..
  35. Haefely W, Kulcsár A, Mohler H. Possible involvement of GABA in the central actions of benzodiazepines. Psychopharmacol Bull. 1975;11:58-9 pubmed
  36. Tang X, Fang H, Li Y, Zhou C, Ren Y, Chen R, et al. Endogenous hydrogen sulfide is involved in asymmetric dimethylarginine-induced protection against neurotoxicity of 1-methyl-4-phenyl-pyridinium ion. Neurochem Res. 2011;36:2176-85 pubmed publisher
    ..Our findings suggest that modulation of H?S production provide new therapeutic targets for the treatment of neurodegenerative disease, such as Parkinson's disease...
  37. Tsukamoto K, Sved A. Contrasting effects of the GABA transaminase inhibitors gamma-vinylGABA and aminooxyacetic acid on arterial pressure following injection into nucleus tractus solitarius. Neuropharmacology. 1993;32:575-9 pubmed
    ..Two typical GABA-transaminase inhibitors, gamma-vinylGABA (GVG) and aminooxyacetic acid (AOAA), increased arterial pressure when injected into the NTS, a response similar to that elicited by ..
  38. Mezo G, Szabo I, Kertesz I, Hegedüs R, Orbán E, Leurs U, et al. Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent. J Pept Sci. 2011;17:39-46 pubmed publisher
  39. Eisenhauer B, Hecht S. Site-specific incorporation of (aminooxy)acetic acid into proteins. Biochemistry. 2002;41:11472-8 pubmed
    ..It has also been shown that the elaborated protein can be cleaved chemically at the site containing the modified amino acid...
  40. Townsend D, Hanigan M. Inhibition of gamma-glutamyl transpeptidase or cysteine S-conjugate beta-lyase activity blocks the nephrotoxicity of cisplatin in mice. J Pharmacol Exp Ther. 2002;300:142-8 pubmed
    ..GGT was inhibited by pretreating the mice with acivicin. Cysteine S-conjugate beta-lyase was inhibited by aminooxyacetic acid (AOAA). Male C57BL/6 mice were treated with 15 mg/kg cisplatin (i.p.) and sacrificed on day 5...
  41. Lee Y, Kang I, Bunger R, Kang Y. Mechanisms of pyruvate inhibition of oxidant-induced apoptosis in human endothelial cells. Microvasc Res. 2003;66:91-101 pubmed
    ..Furthermore, it is suggested that stabilizing the expression of bcl-2 and bax genes by metabolic antioxidants may be an effective strategy for endothelial protection against oxidative stress...
  42. Sakurai T, Kojima C, Ochiai M, Ohta T, Sakurai M, Waalkes M, et al. Cellular glutathione prevents cytolethality of monomethylarsonic acid. Toxicol Appl Pharmacol. 2004;195:129-41 pubmed
    ..GST) that catalyses GSH-substrate conjugation, also enhanced the cytolethality of MMAs(V), but aminooxyacetic acid (AOAA), an inhibitor of beta-lyase that catalyses the final breakdown of GSH-substrate conjugates, had no ..
  43. Steinite I, Gailite A, Ievinsh G. Reactive oxygen and ethylene are involved in the regulation of regurgitant-induced responses in bean plants. J Plant Physiol. 2004;161:191-6 pubmed
    ..demonstrate if the increase of oxidative metabolism was ethylene-dependent, seedlings were pretreated with aminooxyacetic acid, an inhibitor of ethylene biosynthesis, and 1-methylcyclopropene (1-MCP), a competitive inhibitor of ..
  44. Campos Sepulveda A, Martinez Enriquez M, Rodríguez Arellanes R, Peláez L, Rodríguez Amézquita A, Cadena Razo A. Neonatal monosodium glutamate administration increases aminooxyacetic acid (AOA) susceptibility effects in adult mice. Proc West Pharmacol Soc. 2009;52:72-4 pubmed
    ..b>Aminooxyacetic acid (AOAA) is a potent inhibitor of GABA-transaminase and increases GABA levels in the brain...
  45. Paul V, Krishnamoorthy M. The effect of beta-adrenoceptor antagonists alone and in combination with a GABA-elevating agent on isoniazid-induced convulsions in rats. Indian J Physiol Pharmacol. 1989;33:175-8 pubmed
    ..was found to be enhanced in animals pretreated with a gamma-aminobutyric acid (GABA) elevating agent, aminooxyacetic acid (AOAA)...
  46. Elfarra A, Krause R. S-(1,2,2-trichlorovinyl)-L-cysteine sulfoxide, a reactive metabolite of S-(1,2,2-Trichlorovinyl)-L-cysteine formed in rat liver and kidney microsomes, is a potent nephrotoxicant. J Pharmacol Exp Ther. 2007;321:1095-101 pubmed
    ..Furthermore, pretreatment with aminooxyacetic acid enhanced TCVC toxicity...
  47. Liu W, Peterson P, Carter R, Zhou X, Langston J, Fisher A, et al. Crystal structures of unbound and aminooxyacetate-bound Escherichia coli gamma-aminobutyrate aminotransferase. Biochemistry. 2004;43:10896-905 pubmed
    ..Active site structure comparisons with pig gamma-aminobutyrate aminotransferase and dialkylglycine decarboxylase are discussed...
  48. Novelli M, Fabregat M, Fernandez Alvarez J, Gomis R, Masiello P. Metabolic and functional studies on isolated islets in a new rat model of type 2 diabetes. Mol Cell Endocrinol. 2001;175:57-66 pubmed
  49. Chan E, Park S, Yousaf M. An electroactive catalytic dynamic substrate that immobilizes and releases patterned ligands, proteins, and cells. Angew Chem Int Ed Engl. 2008;47:6267-71 pubmed publisher
  50. Austgen J, Hermann G, Dantzler H, Rogers R, Kline D. Hydrogen sulfide augments synaptic neurotransmission in the nucleus of the solitary tract. J Neurophysiol. 2011;106:1822-32 pubmed publisher
    ..Taken together, these data support a presynaptic role for endogenous H?S in modulation of excitatory neurotransmission in the NTS...
  51. González J, Caballero A, Viegas I, Metón I, Jones J, Barra J, et al. Effects of alanine aminotransferase inhibition on the intermediary metabolism in Sparus aurata through dietary amino-oxyacetate supplementation. Br J Nutr. 2012;107:1747-56 pubmed publisher
    ..The present study indicates that AOA-dependent inhibition of the cytosolic ALT activity could help to increase the use of dietary carbohydrate nutrients...
  52. Chmiel Perzyńska I, Perzynski A, Wielosz M, Urbanska E. Hyperglycemia enhances the inhibitory effect of mitochondrial toxins and D,L-homocysteine on the brain production of kynurenic acid. Pharmacol Rep. 2007;59:268-73 pubmed
    ..of kynurenic acid (KYNA) production exerted by mitochondrial toxins: 3-nitropropionic acid (3-NPA) and aminooxyacetic acid (AOAA), by endogenous agonists of glutamate receptors: L-glutamate and L-cysteine sulfinate, and by a risk ..
  53. Xu Z, Yu X, Feng X, Bao M. Oxidative coupling of indoles with ethyl 2-(disubstituted amino)acetates: an approach to achieve indolylglycine derivatives. J Org Chem. 2012;77:7114-8 pubmed publisher