Query Query
Results
Date
16 reactions in Reaxys
2018-01-01 07h:44m:17s (EST)
O OH GH
GH
1. Query
NH 2
GH
NH 2
GH GH
GH N
GH GH
GH
N
GH GH
GH
Search as: As drawn, No salts, No mixtures
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
1/8
2018-01-01 08:04:51
NH
NH
H
Cl
H
NH 2 NH 2
OH
O
Rx-ID: 46333663 View in Reaxys 1/16 Yield
Conditions & References
23.3 %
Synthesis of Tryptamine Hydrochloride Mixtures of equimolar 0.01 pyridoxal hydrochloride and D-tryptophan in a 90percent buffer solution were kept for 18 h at T = 15 °C. In preparing the solutions, the mixtures turned an intense yellow and changed their color to orange over time. The color then became less intense, and a white precipitate formed. The precipitate was filtered off, washed with alcohol, and dried to a constant weight. The yield was 0.0088 g (23.3percent); m > 210 °C (the precipitate blackened as it decomposed). The product yielded a qualitative reaction for Cl− with a solution of AgNO3 and aqualitative reaction with Br2 (violet). The final product was poorly soluble in alcohol (IR spectrum (KBr), ν, cm−1: 3150– 3350 (NH2), 2250–2700 (>NH), 1625, 1580 (C=C); UV spectrum, λmax: 280 nm). With pyridoxal hydrochloride in aq. buffer, Time= 18h, T= 15 °C Pishchugin; Tuleberdiev; Russian Journal of Physical Chemistry A; vol. 91; nb. 10; (2017); p. 1851 - 1854; Zh. Fiz. Khim.; vol. 91; nb. 10; (2017); p. 1648 - 1652,5 View in Reaxys
NH
NH NH 2
O
OH
NH 2
Rx-ID: 3829957 View in Reaxys 2/16 Yield 63 %
Conditions & References in diphenylether, Time= 10h, Heating Biswas, Kshetra M.; Jackson, Anthony H.; Kobaisy, Mozaina M.; Shannon, Patrick V. R.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1992); p. 461 - 468 View in Reaxys 5.4 Kinetic analysis General procedure: Reaction mixtures of 50μl assays containing recombinant protein (25μg for P. somniferum TyDC 5-hydroxytryptophan, 3μg for the P. somniferum TyDC dopa, 25μg for C. roseus TDC dopa and 3μg for the C. roseus TDC tryptophan) and varying concentration of substrate (0.05–20mM of 5-hydroxytryptophan, 0.005–5mM of tryptophan and 0.05–15mM of dopa) were prepared in 50mM phosphate buffer (pH 7.5) and incubated at 25°C. An equal volume of 0.8M HCO2H was added to each reaction mixture (15min for P. somniferum TyDC 5-hydroxytryptophan assays, 2.5min for P. somniferum dopa assays, 15min for C. roseus TDC dopa assays and 2.5min for C. roseus tryptophan assays) with supernatants individually was subjected to HPLC-electrochemical analysis. Kinetic data points were performed in triplicate and kinetic values were evaluated by hyperbolic regression. An isocratic running buffer consisting of 50mM phosphate buffer pH 4.3, 25percent acetonitrile, and 0.5mM octyl sulfate was used for the 5hydroxytryptophan characterization, whereas an isocratic running buffer consisting of 50mM phosphate buffer pH 4.3, 15percent acetonitrile, and 0.5mM octyl sulfate was used for the dopa characterization. The amounts of products in reaction mixtures containing different concentrations of substrate were quantified based on a standard curve generated using authentic standards at identical conditions of HPLC-electrochemical analysis. With Catharanthus roseus tryptophan decarboxylase in aq. phosphate buffer, T= 25 °C , pH= 7.5, Enzymatic reaction, Kinetics, Reagent/catalyst Torrens-Spence, Michael P.; Lazear, Michael; Von Guggenberg, Renee; Ding, Haizhen; Li, Jianyong; Phytochemistry; vol. 106; (2014); p. 37 - 43 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/8
2018-01-01 08:04:51
NH
NH
HO
NH 2
O
HO
OH
NH 2
Rx-ID: 3846062 View in Reaxys 3/16 Yield
Conditions & References With pyridoxal 5'-phosphate, mammalian aromatic L-amino acid decarboxylase Battersby; Scott; Staunton; Tetrahedron; vol. 46; nb. 13-14; (1990); p. 4685 - 4696 View in Reaxys 5.4 Kinetic analysis General procedure: Reaction mixtures of 50μl assays containing recombinant protein (25μg for P. somniferum TyDC 5-hydroxytryptophan, 3μg for the P. somniferum TyDC dopa, 25μg for C. roseus TDC dopa and 3μg for the C. roseus TDC tryptophan) and varying concentration of substrate (0.05–20mM of 5-hydroxytryptophan, 0.005–5mM of tryptophan and 0.05–15mM of dopa) were prepared in 50mM phosphate buffer (pH 7.5) and incubated at 25°C. An equal volume of 0.8M HCO2H was added to each reaction mixture (15min for P. somniferum TyDC 5-hydroxytryptophan assays, 2.5min for P. somniferum dopa assays, 15min for C. roseus TDC dopa assays and 2.5min for C. roseus tryptophan assays) with supernatants individually was subjected to HPLC-electrochemical analysis. Kinetic data points were performed in triplicate and kinetic values were evaluated by hyperbolic regression. An isocratic running buffer consisting of 50mM phosphate buffer pH 4.3, 25percent acetonitrile, and 0.5mM octyl sulfate was used for the 5hydroxytryptophan characterization, whereas an isocratic running buffer consisting of 50mM phosphate buffer pH 4.3, 15percent acetonitrile, and 0.5mM octyl sulfate was used for the dopa characterization. The amounts of products in reaction mixtures containing different concentrations of substrate were quantified based on a standard curve generated using authentic standards at identical conditions of HPLC-electrochemical analysis. With Papaver somniferum tyrosine decarboxylase S372G mutant in aq. phosphate buffer, T= 25 °C , pH= 7.5, Enzymatic reaction, Kinetics, Reagent/catalyst Torrens-Spence, Michael P.; Lazear, Michael; Von Guggenberg, Renee; Ding, Haizhen; Li, Jianyong; Phytochemistry; vol. 106; (2014); p. 37 - 43 View in Reaxys
O H 2N
OH
NH
H
Cl
H
NH 2
N H
Rx-ID: 38715371 View in Reaxys 4/16 Yield 72 %
Conditions & References General “One-Pot” Procedure for the Decarboxylation of Amino Acids General procedure: General “One-Pot” Procedure for the Decarboxylation of Amino Acids [0045] A magnetic stir bar, 3 mL of n-PrOH, 10 mmol of R-Carvone, and 5 mmol of amino acid were charged to a pressure vessel. The vessel was heated from room temperature to 190° C. over 5 min with stirring. If necessary the reaction vessel was maintained at 190° C. for additional time until the slurry became clear. The vessel was allowed to cool to below the solvent boiling point, carefully vented to release evolved CO2, and 10 mL of 2M HCl was added. The vessel was heated to 190° C. over 5 min with stirring and allowed to cool. The aqueous reaction mixture was washed three times with 25 mL of ether and water solvent distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150° C. and 10 Torr. The hydrochloride salt was then weighed and analyzed via IR and NMR.; tryptamine hydrochloride, δH 2.97 2H t J=9, 3.13 2H t J=8, 7.01 1H t J=4, 7.07-7.12 2H m, 7.34 1H d J=4, 7.49 1H d J=4; δC 22.88, 40.03, 109.36, 112.30, 118.54, 119.68, 122.44, 124.53, 126.70, 136.69 Stage 1: With (-)-Carvone in propan-1-ol, Time= 0.15h, T= 190 °C , p= 11251.1Torr , Sealed tube Stage 2: With hydrogenchloride in propan-1-ol, water, Time= 0.0833333h, T= 190 °C Patent; Morrison, Richard W.; Jackson, Douglas Michael; US2014/275569; (2014); (A1) English View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/8
2018-01-01 08:04:51
O
OH NH
H 2N
H OH
HO
NH 2
HN
Rx-ID: 3846071 View in Reaxys 5/16 Yield
Conditions & References
97 %
With pyridoxal 5'-phosphate, aromatic L-amino acid decarboxylase in various solvent(s), Time= 48h, T= 30 °C Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji; Bioscience, Biotechnology, and Biochemistry; vol. 57; nb. 7; (1993); p. 1210 - 1211 View in Reaxys With NH4OH-NH4Cl buffer, pyridoxal 5'-phosphate, Time= 0.5h, T= 30 °C , relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 45; nb. 11; (1981); p. 2543 - 2552 View in Reaxys With isopropyl β-D-thiogalactoside, L-tryptophan decarboxylase in recombinant Escherichia coli, T= 28 °C Park, Munyoung; Kang, Kiyoon; Park, Sangkyu; Back, Kyoungwhan; Bioscience, Biotechnology and Biochemistry; vol. 72; nb. 9; (2008); p. 2456 - 2458 View in Reaxys With aromatic L-amino acid decarboxylase, Enzymatic reaction Wood, Irene; Martini, M. Florencia; Pickholz, Monica; Journal of Molecular Structure; vol. 1045; (2013); p. 124 130 View in Reaxys
NH N S+
N
N
Cl –
NH 2
O
OH
O
NH
NH 2
N
NH 2
O
HN
O
NH 2
HO
HO O O
OH
NH 2
Rx-ID: 36203975 View in Reaxys 6/16 Yield
Conditions & References With Saccharomyces cerevisiae wild type strain V328, Time= 0.333333h, UV-irradiation Bracchitta, Giuseppina; Catalfo, Alfio; De Guidi, Guido; Photochemical and Photobiological Sciences; vol. 12; nb. 6; (2013); p. 967 - 973 View in Reaxys
NH O
NH
O
N
NH 2
HO
O
OH
NH 2
OH
Rx-ID: 36203976 View in Reaxys 7/16 Yield
Conditions & References With Saccharomyces cerevisiae wild type strain V328, Time= 0.333333h, UV-irradiation
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/8
2018-01-01 08:04:51
Bracchitta, Giuseppina; Catalfo, Alfio; De Guidi, Guido; Photochemical and Photobiological Sciences; vol. 12; nb. 6; (2013); p. 967 - 973 View in Reaxys
O H 2N
OH
NH
H
NH 2
N H
Rx-ID: 3830113 View in Reaxys 8/16 Yield
Conditions & References
98 %
With pyridoxal 5'-phosphate, aromatic L-amino acid decarboxylase in various solvent(s), Time= 48h, T= 30 °C Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji; Bioscience, Biotechnology, and Biochemistry; vol. 57; nb. 7; (1993); p. 1210 - 1211 View in Reaxys
92.3 %
With cyclohexenon in various solvent(s), Time= 1.5h, T= 154 °C Hashimoto, Mitsunori; Eda, Yutaka; Osanai, Yasutomo; Iwai, Toshiaki; Aoki, Seiichi; Chemistry Letters; (1986); p. 893 - 896 View in Reaxys With L-amino acid decarboxylase from Micrococcus percitreus AJ 1065, NH4OH-NH4Cl buffer, pyridoxal 5'-phosphate in water, Time= 0.5h, T= 30 °C , study of the inhibition of the enzyme by various amino acids and amines, inhibition of L-dopa in different buffer solutions, Product distribution Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 51; nb. 9; (1987); p. 2531 - 2538 View in Reaxys With NH4OH-NH4Cl buffer, pyridoxal 5'-phosphate, Time= 0.5h, T= 30 °C , relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 45; nb. 11; (1981); p. 2543 - 2552 View in Reaxys With isopropyl β-D-thiogalactoside, L-tryptophan decarboxylase in recombinant Escherichia coli, Time= 24h, T= 28 °C Park, Munyoung; Kang, Kiyoon; Park, Sangkyu; Back, Kyoungwhan; Bioscience, Biotechnology and Biochemistry; vol. 72; nb. 9; (2008); p. 2456 - 2458 View in Reaxys With tryptophan decarboxylase from Catharanthus roseus (Madagascar periwinkle), pyridoxal 5'-phosphate, 2-hydroxyethanethiol, T= 30 °C , pH= 8.5, aq. phosphate buffer, Enzymatic reaction, Kinetics Runguphan, Weerawat; Qu, Xudong; O'Connor, Sarah E.; Nature; vol. 468; nb. 7322; (2010); p. 461 - 467 View in Reaxys
H 2N
O OH
NH
Cl Cl
N H
NH 2
Rx-ID: 33075313 View in Reaxys 9/16 Yield
Conditions & References With tryptophan decarboxylase from Catharanthus roseus (Madagascar periwinkle), pyridoxal 5'-phosphate, 2-hydroxyethanethiol, T= 30 °C , pH= 8.5, aq. phosphate buffer, Enzymatic reaction, Kinetics
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/8
2018-01-01 08:04:51
Runguphan, Weerawat; Qu, Xudong; O'Connor, Sarah E.; Nature; vol. 468; nb. 7322; (2010); p. 461 - 467 View in Reaxys
Cl
O
NH
OH H 2N
H
NH
NH 2
Cl
Rx-ID: 33075314 View in Reaxys 10/16 Yield
Conditions & References With tryptophan decarboxylase from Catharanthus roseus (Madagascar periwinkle), pyridoxal 5'-phosphate, 2-hydroxyethanethiol, T= 30 °C , pH= 8.5, aq. phosphate buffer, Enzymatic reaction, Kinetics Runguphan, Weerawat; Qu, Xudong; O'Connor, Sarah E.; Nature; vol. 468; nb. 7322; (2010); p. 461 - 467 View in Reaxys
O
OH
H 2N
NH
H
H
NH 2 O
NH 2
HO O
NH 2
N H
O
O
O
OH
NH 2
HO
O
O
HN
O
H 2N
H
H 2N
OH H
OH
HO
HN N H
OH
NH
NH 2
O
OH
O HN
HN
O OH
Rx-ID: 29255151 View in Reaxys 11/16 Yield
Conditions & References With dihydrogen peroxide, Time= 6h, T= 37 °C , pH= 4.6, Darkness, aq. borate buffer Salminen, Hanna; Heinonen, Marina; Journal of Agricultural and Food Chemistry; vol. 56; nb. 16; (2008); p. 7472 7481 View in Reaxys
O
H 14 2 C
OH H 2N
NH 2
H
H 14 C 2
NH NH
Rx-ID: 11193514 View in Reaxys 12/16 Yield
Conditions & References With hydrogenchloride, tryptophan (trp), Tris buffer, pyridoxal 5'-phosphate, Time= 48h, T= 37 °C , pH= 5.5 Wigley, Lucy J.; Mantle, Peter G.; Perry, David A.; Phytochemistry; vol. 67; nb. 6; (2006); p. 561 - 569 View in Reaxys
NH
NH NH 2
O
OH
NH 2
Rx-ID: 2053851 View in Reaxys 13/16 Yield 12 %
Conditions & References With pyridoxal 5'-phosphate, aromatic L-amino acid decarboxylase in various solvent(s), Time= 48h, T= 30 °C
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
6/8
2018-01-01 08:04:51
Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji; Bioscience, Biotechnology, and Biochemistry; vol. 57; nb. 7; (1993); p. 1210 - 1211 View in Reaxys With NH4OH-NH4Cl buffer, pyridoxal 5'-phosphate, Time= 0.5h, T= 30 °C , relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 45; nb. 11; (1981); p. 2543 - 2552 View in Reaxys
NH
NH
F
NH 2
F
OH
O
NH 2
Rx-ID: 2120483 View in Reaxys 14/16 Yield
Conditions & References
41 %
With pyridoxal 5'-phosphate, aromatic L-amino acid decarboxylase in various solvent(s), Time= 48h, T= 30 °C Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji; Bioscience, Biotechnology, and Biochemistry; vol. 57; nb. 7; (1993); p. 1210 - 1211 View in Reaxys With NH4OH-NH4Cl buffer, pyridoxal 5'-phosphate, Time= 0.5h, T= 30 °C , relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 45; nb. 11; (1981); p. 2543 - 2552 View in Reaxys
NH
NH NH 2
Cl
OH
O
H
NH 2
Rx-ID: 3829960 View in Reaxys 15/16 Yield
Conditions & References
90 %
With hydrogenchloride in various solvent(s), Time= 0.333333h, Heating Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 21; nb. 4; (1985); p. 502 - 509; Khimiya Prirodnykh Soedinenii; vol. 21; nb. 4; (1985); p. 536 - 544 View in Reaxys
72 %
With hydrogenchloride in various solvent(s), Time= 0.333333h, Heating Tulyaganov, T. S.; Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 17; (1981); p. 149 152; Khimiya Prirodnykh Soedinenii; vol. 17; nb. 2; (1981); p. 192 - 195 View in Reaxys
NH
H
Cl
H
H
O
H
O
OH
NH 2
O O
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
7/8
OH
2018-01-01 08:04:51
NH
O HO
H 2N
NH 2
O
O HO
OH
OH
OH O
NH 2
NH 2
Rx-ID: 5701012 View in Reaxys 16/16 Yield
Conditions & References Akabori; Narita; Proceedings of the Japan Academy; vol. 25; nb. 11; (1949); p. 6 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
8/8
2018-01-01 08:04:51