[DB] 2-Amino-3-(1,2,4,5,6,7-hexa'GH'-1H-indol-3-yl)propanoic acid to

Page 1

Bioactivities (10879)

Yield

Reactions (16)

Substances (35)

Targets (841)

Citations (18)

Conditions

References

1

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Rx-ID: 3829957

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in diphenylether

10 h; 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), 1992 , # 4 p. 461 - 468 Title/Abstract Full Text View citing articles Show Details

With Catharanthus roseus tryptophan decarboxylase in aq. phosphate buffer

T=25°C; pH=7.5; Enzymatic reaction; Kinetics; Reagent/catalyst; Hide Experimental Procedure

Torrens-Spence, Michael P.; Lazear, Michael; Von Guggenberg, Renee; Ding, Haizhen; Li, Jianyong

Phytochemistry, 2014 , vol. 106, p. 37 - 43 Title/Abstract Full Text Show Details

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 5-hydroxytryptophan 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.


2

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Rx-ID: 3830113

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98%

With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase in various solvent(s) T=30°C; 48 h;

Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji

Bioscience, Biotechnology, and Biochemistry, 1993 , vol. 57, # 7 p. 1210 - 1211 Title/Abstract Full Text Show Details

92.3%

With cyclohexenon in various solvent(s) T=154°C; 1.5 h;

Hashimoto, Mitsunori; Eda, Yutaka; Osanai, Yasutomo; Iwai, Toshiaki; Aoki, Seiichi

Chemistry Letters, 1986 , p. 893 - 896 Title/Abstract Full Text Show Details

With L-amino acid decarboxylase from Micrococcus percitreus AJ 1065; NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate in water

T=30°C; 0.5 h; 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, 1987 , vol. 51, # 9 p. 2531 - 2538 Title/Abstract Full Text Show Details

With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate

T=30°C; 0.5 h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;

Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki

Agricultural and Biological Chemistry, 1981 , vol. 45, # 11 p. 2543 - 2552 Title/Abstract Full Text Show Details

With isopropyl β-D-thiogalactoside; L-tryptophan decarboxylase in recombinant Escherichia coli T=28°C; 24 h;

Park, Munyoung; Kang, Kiyoon; Park, Sangkyu; Back, Kyoungwhan

Bioscience, Biotechnology and Biochemistry, 2008 , vol. 72, # 9 p. 2456 - 2458 Title/Abstract Full Text View citing articles Show Details

With tryptophan decarboxylase from Catharanthus roseus (Madagascar periwinkle); pyridoxal 5'-phosphate; 2-hydroxyethanethiol

T=30°C; pH=8.5; aq. phosphate bufferEnzymatic reaction; Kinetics;

Runguphan, Weerawat; Qu, Xudong; O'Connor, Sarah E.

Nature, 2010 , vol. 468, # 7322 p. 461 - 467 Title/Abstract Full Text View citing articles Show Details

A

B

C

D

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3

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Akabori; Narita

Proceedings of the Japan Academy, 1949 , vol. 25, # 11 p. 6 Full Text View citing articles Show Details


A

B

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4

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Rx-ID: 36203976

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With Saccharomyces cerevisiae wild type strain V328

0.333333 h; UV-irradiation;

Bracchitta, Giuseppina; Catalfo, Alfio; De Guidi, Guido

Photochemical and Photobiological Sciences, 2013 , vol. 12, # 6 p. 967 - 973 Title/Abstract Full Text View citing articles Show Details

5

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Rx-ID: 11193514

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With hydrogenchloride; tryptophan (trp); Tris buffer; pyridoxal 5'-phosphate

T=37°C; pH=5.5; 48 h;

Wigley, Lucy J.; Mantle, Peter G.; Perry, David A.

Phytochemistry, 2006 , vol. 67, # 6 p. 561 - 569 Title/Abstract Full Text View citing articles Show Details

6

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Rx-ID: 2053851

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With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase in various solvent(s) T=30°C; 48 h;

Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji

Bioscience, Biotechnology, and Biochemistry, 1993 , vol. 57, # 7 p. 1210 - 1211 Title/Abstract Full Text Show Details

With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate

T=30°C; 0.5 h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;

Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki

Agricultural and Biological Chemistry, 1981 , vol. 45, # 11 p. 2543 - 2552 Title/Abstract Full Text Show Details


7

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Rx-ID: 3846062

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With pyridoxal 5'-phosphate

mammalian aromatic L-amino acid decarboxylase;

Battersby; Scott; Staunton

Tetrahedron, 1990 , vol. 46, # 13-14 p. 4685 - 4696 Title/Abstract Full Text View citing articles Show Details

With Papaver somniferum tyrosine decarboxylase S372G mutant in aq. phosphate buffer

T=25°C; pH=7.5; Enzymatic reaction; Kinetics; Reagent/catalyst; Hide Experimental Procedure

Torrens-Spence, Michael P.; Lazear, Michael; Von Guggenberg, Renee; Ding, Haizhen; Li, Jianyong

Phytochemistry, 2014 , vol. 106, p. 37 - 43 Title/Abstract Full Text Show Details

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 5-hydroxytryptophan 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.

8

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Rx-ID: 3846071

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With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase in various solvent(s) T=30°C; 48 h;

Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji

Bioscience, Biotechnology, and Biochemistry, 1993 , vol. 57, # 7 p. 1210 - 1211 Title/Abstract Full Text Show Details

With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate

T=30°C; 0.5 h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;

Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki

Agricultural and Biological Chemistry, 1981 , vol. 45, # 11 p. 2543 - 2552 Title/Abstract Full Text Show Details

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, 2008 , vol. 72, # 9 p. 2456 - 2458 Title/Abstract Full Text View citing articles Show Details

With aromatic L-amino acid decarboxylase

Enzymatic reaction;

Wood, Irene; Martini, M. Florencia; Pickholz, Monica

Journal of Molecular Structure, 2013 , vol. 1045, p. 124 - 130 Title/Abstract Full Text View citing articles Show Details


9

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Rx-ID: 2120483

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With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase in various solvent(s) T=30°C; 48 h;

Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji

Bioscience, Biotechnology, and Biochemistry, 1993 , vol. 57, # 7 p. 1210 - 1211 Title/Abstract Full Text Show Details

With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate

T=30°C; 0.5 h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;

Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki

Agricultural and Biological Chemistry, 1981 , vol. 45, # 11 p. 2543 - 2552 Title/Abstract Full Text Show Details

10

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Rx-ID: 33075313

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With tryptophan decarboxylase from Catharanthus roseus (Madagascar periwinkle); pyridoxal 5'-phosphate; 2-hydroxyethanethiol

T=30°C; pH=8.5; aq. phosphate bufferEnzymatic reaction; Kinetics;

Runguphan, Weerawat; Qu, Xudong; O'Connor, Sarah E.

Nature, 2010 , vol. 468, # 7322 p. 461 - 467 Title/Abstract Full Text View citing articles Show Details

11

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Rx-ID: 33075314

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With tryptophan decarboxylase from Catharanthus roseus (Madagascar periwinkle); pyridoxal 5'-phosphate; 2-hydroxyethanethiol

T=30°C; pH=8.5; aq. phosphate bufferEnzymatic reaction; Kinetics;

Runguphan, Weerawat; Qu, Xudong; O'Connor, Sarah E.

Nature, 2010 , vol. 468, # 7322 p. 461 - 467 Title/Abstract Full Text View citing articles Show Details


12

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Rx-ID: 3829960

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90%

With hydrogenchloride in various solvent(s) 0.333333 h; Heating;

Ibragimov, A. A.; Yunusov, S. Yu.

Chemistry of Natural Compounds, 1985 , vol. 21, # 4 p. 502 - 509 Khimiya Prirodnykh Soedinenii, 1985 , vol. 21, # 4 p. 536 - 544 Title/Abstract Full Text View citing articles Show Details

72%

With hydrogenchloride in various solvent(s) 0.333333 h; Heating;

Tulyaganov, T. S.; Ibragimov, A. A.; Yunusov, S. Yu.

Chemistry of Natural Compounds, 1981 , vol. 17, p. 149 - 152 Khimiya Prirodnykh Soedinenii, 1981 , vol. 17, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details

13

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72%

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Rx-ID: 38715371

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Stage #1: With (-)-Carvone in propan-1-ol

T=190°C; P=11251.1 Torr; 0.15 h; Sealed tube; Stage #2: With hydrogenchloride in propan-1-ol; water

T=190°C; 0.0833333 h; Hide Experimental Procedure

Morrison, Richard W.; Jackson, Douglas Michael

Patent: US2014/275569 A1, 2014 ; Location in patent: Page/Page column 0045; 0053; 0066; 0067 ; Title/Abstract Full Text Show Details

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

14

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Rx-ID: 46333663


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With pyridoxal hydrochloride in aq. buffer T=15°C; 18 h; Hide Experimental Procedure

Pishchugin; Tuleberdiev

Russian Journal of Physical Chemistry A, 2017 , vol. 91, # 10 p. 1851 - 1854 Zh. Fiz. Khim., 2017 , vol. 91, # 10 p. 1648 - 1652,5 Title/Abstract Full Text View citing articles Show Details

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). A

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C

D

E

F

G

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15

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Salminen, Hanna; Heinonen, Marina

Journal of Agricultural and Food Chemistry, 2008 , vol. 56, # 16 p. 7472 - 7481 Title/Abstract Full Text View citing articles Show Details

With dihydrogen peroxide

T=37°C; pH=4.6; 6 h; Darknessaq. borate buffer;

A

B

C

D

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16

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With Saccharomyces cerevisiae wild type strain V328

0.333333 h; UV-irradiation;

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Bracchitta, Giuseppina; Catalfo, Alfio; De Guidi, Guido

Photochemical and Photobiological Sciences, 2013 , vol. 12, # 6 p. 967 - 973 Title/Abstract Full Text View citing articles Show Details


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