N-acetyltryptophan methyl ester
A
N-AcTrp
B
AcTrpOMe
Conditions | Yield |
---|---|
With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4 In tetrahydrofuran Ambient temperature; | A 99% B 99% |
With methanol; water; α-chymotrypsin bei pH 7.8; |
Conditions | Yield |
---|---|
With sodium hydroxide In acetone at 20℃; pH=> 10; | 80% |
Conditions | Yield |
---|---|
Stage #1: tiolacetic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: L-Tryptophan With 2,4-Dinitrofluorobenzene In N,N-dimethyl-formamide at 20℃; for 3h; | 76% |
Conditions | Yield |
---|---|
With sodium In water for 2h; | 73% |
Stage #1: L-Tryptophan With sodium hydroxide In water for 0.5h; Stage #2: acetic anhydride In water at 20℃; | 71.8% |
With sodium hydroxide; water |
Conditions | Yield |
---|---|
With ammonium bicarbonate; water In dichloromethane for 21h; α-chymotrypsin; | 45% |
With α-chymotrypsin In phosphate buffer at 25℃; pH=7.8; Kinetics; Further Variations:; Reaction partners; Catalysts; Hydrolysis; Enzymatic reaction; |
acetyltryptophan ethylester
A
N-AcTrp
B
N-acetyl-D-tryptophan
C
N-acetyl-D-tryptophan ethyl ester
Conditions | Yield |
---|---|
With water In ethanol at 25℃; for 24h; Microbiological reaction; optical yield given as %ee; enantioselective reaction; | A n/a B n/a C 40% |
N-acetyl-DL-tryptophan
N-AcTrp
Conditions | Yield |
---|---|
With (S)-1-phenyl-ethylamine | |
With (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol | |
With (1S,2S)-(+)-thiomicamine |
Conditions | Yield |
---|---|
With water bei der Einwirkung einer Amidase; | |
mit Hilfe von Amidase aus Penicillium vinaceum oder Aspergillus orizae; | |
mit Hilfe von Pseudomonas; | |
With water bei der Einwirkung einer Amidase; |
(Z)-2-acetamido-3-(3-indolyl)-2-propenoic acid
A
N-AcTrp
B
N-acetyl-D-tryptophan
Conditions | Yield |
---|---|
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (-)-Diop In ethanol at 50℃; for 1.75h; Title compound not separated from byproducts; | |
With hydrogen; triethylamine; ClO4; (2S,4S)-MOD-BPPM In ethanol at 50℃; under 15200 Torr; for 20h; Title compound not separated from byproducts; |
N-acetyl-L-triptophanyl-L-leucine amide
A
H-L-Leu-NH2
B
N-AcTrp
Conditions | Yield |
---|---|
With pH=7; α-chymotrypsin In water; ethyl acetate Equilibrium constant; |
(S)-2-Acetylamino-5-(phenyl-hydrazono)-pentanoic acid methyl ester
N-AcTrp
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide 1.) reflux, 1 h;; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
β‐cyclodextrin In water; dimethyl sulfoxide at 25℃; Rate constant; Mechanism; various conditions; |
Conditions | Yield |
---|---|
With Peptidamidase aus dem Flavedo von Orangen; water at 30℃; diff. Peptidamiden; diff. solvents; diff. pH; | |
With potassium phosphate buffer at 30℃; for 1h; amidase from Erwina carotovora; determination of relative rate of deamination; | |
With water at 30℃; Peptidamidase aus dem Flavedo von Orangen; Yield given; | |
With subtilisin-CLEC at 40℃; pH 7.5, phosphate buffer; Yield given; |
N-acetyl-L-tryptophan methyl ester
A
methanol
B
N-AcTrp
Conditions | Yield |
---|---|
With water In dimethyl sulfoxide at 35℃; Rate constant; Equilibrium constant; pH 5.0, pH 7.1; influence of enzyme chymotrypsin; influence of BzPheal=Ala; |
(S)-2-Acetylamino-4-cyano-butyric acid methyl ester
N-AcTrp
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / hydrogen / Raney-Ni deactivated with 3percent Pb / H2O; acetic acid 3: 1.) 0.1 N HCl; 2.) 1 N NaOH / 1.) reflux, 1 h; View Scheme |
methyl 2-acetamido-5-amino-5-oxopentanoate
N-AcTrp
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 61 percent / p-TsCl / pyridine 2: 88 percent / hydrogen / Raney-Ni deactivated with 3percent Pb / H2O; acetic acid 4: 1.) 0.1 N HCl; 2.) 1 N NaOH / 1.) reflux, 1 h; View Scheme |
(2S,5R)-1-Acetyl-5-hydroxy-pyrrolidine-2-carboxylic acid methyl ester
N-AcTrp
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 1.) 0.1 N HCl; 2.) 1 N NaOH / 1.) reflux, 1 h; View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous K2CO3 2: α-chymotrypsin; methanol; water / bei pH 7.8 View Scheme |
Conditions | Yield |
---|---|
With acetic anhydride In water |
Conditions | Yield |
---|---|
Stage #1: Fmoc-Trp-OH With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Wang resin; Inert atmosphere; Stage #2: acetic acid With ammonium bicarbonate In methanol at 20℃; for 3h; Stage #3: With piperidine; trifluoroacetic acid In N,N-dimethyl-formamide at 20℃; Inert atmosphere; |
N-Acetyl-N(1)-nitroso-L-tryptophan
N-AcTrp
Conditions | Yield |
---|---|
With L-Cysteine In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Kinetics; |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 24.84℃; pH=8.5 - 9; Kinetics; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 23h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2; | 98% |
With hydrogenchloride; water | |
With sulfuric acid; water | |
With Aspergillus oryzae acylase relative rates; |
sodium thiocyanide
acetic anhydride
N-AcTrp
(S)-5-((1H-indol-3-yl)methyl)-1-acetyl-2-thioxoimidazolidin-4-one
Conditions | Yield |
---|---|
In acetic acid at 80 - 85℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
Stage #1: N-AcTrp With N-chlorobenzotriazole; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.25h; Stage #2: benzylamine With triethylamine at 20℃; for 1.83333h; | 95% |
trans-dihydroxo (2,3,6,7,12,13,16,17-octaethylporphyrinato)-tin(IV)
N-AcTrp
Conditions | Yield |
---|---|
In chloroform for 12h; Reflux; | 92% |
Conditions | Yield |
---|---|
Stage #1: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride With potassium carbonate In water at 25℃; for 0.166667h; Stage #2: N-AcTrp With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h; | 91% |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride In dichloromethane Schlenk technique; | |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride In dichloromethane Schlenk technique; |
trans-dihydroxo(meso-tetraphenylporphyrinato)tin(IV)
N-AcTrp
Conditions | Yield |
---|---|
In chloroform for 12h; Reflux; | 91% |
Conditions | Yield |
---|---|
lipoglycosylated α-chymotrypsin In chloroform at 30℃; or other solvents; | 90% |
α-chymotrypsin In chloroform; water at 30℃; for 24h; phosphate buffer, pH 6.8; | 86% |
α-chymotrypsin at 30℃; for 24h; Equilibrium constant; effect of water concentration, solvent, pH; | 78% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid a) 50 deg C, 0.5 h, b) RT, 4 h; | 90% |
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; | 89% |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: L-valine methylester hydrochloride In dichloromethane Schlenk technique; | |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: L-valine methylester hydrochloride In dichloromethane Schlenk technique; |
Conditions | Yield |
---|---|
Stage #1: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride With potassium carbonate In water at 25℃; for 0.166667h; Stage #2: N-AcTrp With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h; | 89% |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride In dichloromethane Schlenk technique; | |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride In dichloromethane Schlenk technique; |
O-Methyl (S)-prop-2-ynyl dithiocarbonate
N-AcTrp
N-acetyl-L-tryptophan methyl ester
Conditions | Yield |
---|---|
In toluene Heating; | 87% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight; | 87% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight; | 85% |
N-AcTrp
Conditions | Yield |
---|---|
In trifluoroacetic acid Ar, stirred at 50°C for 3 h; concd., pptd. (diethyl ether), washed (methanol/diethyl ether), dried (vac.); elem. anal.; | 84% |
N-AcTrp
N-acetyl-L-tryptophan methyl ester
Conditions | Yield |
---|---|
In toluene Heating; | 81% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight; | 80% |
N-AcTrp
Conditions | Yield |
---|---|
In trifluoroacetic acid (argon); stirring (room temp., 4 h); pptn. with Et2O, washing, drying (vac.); elem. anal.; | 80% |
diazomethane
N-AcTrp
N-acetyl-L-tryptophan methyl ester
Conditions | Yield |
---|---|
In methanol; diethyl ether at 0℃; | 79% |
N-AcTrp
Conditions | Yield |
---|---|
In toluene Heating; | 79% |
Conditions | Yield |
---|---|
Stage #1: methyl (L)-leucinate hydrochloride With potassium carbonate In water at 25℃; for 0.166667h; Stage #2: N-AcTrp With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h; | 79% |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: methyl (L)-leucinate hydrochloride In dichloromethane Schlenk technique; | |
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique; Stage #2: methyl (L)-leucinate hydrochloride In dichloromethane Schlenk technique; |
N-AcTrp
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 21℃; for 16h; Inert atmosphere; | 77% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 21℃; for 16h; Inert atmosphere; | 77% |
N-methyl-N-[(S)-1-phenylethyl]amine
N-AcTrp
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight; | 76% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight; | 75% |
hexakis-(6-bromo-6-deoxy)-α-cyclodextrin
N-AcTrp
hexakis-[6-O-(N-acetyl-L-tryptophanyl)]-α-cyclodextrin
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 70 - 80℃; for 12h; | 72% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight; | 70% |
Reported in EPA TSCA Inventory.
1. Introduction of N-Acetyl-L-tryptophan
N-Acetyl-L-tryptophan, with the IUPAC Name of 2-Acetamido-3-(1H-indol-3-yl)propanoic acid, is one kind of white crystalline powder, odorless, little bitter taste. And it belongs to the Classification Code which include Drug / Therapeutic Agent; Enzyme Inhibitors; Protease Inhibitors; Reproductive Effect.
2. Properties of N-Acetyl-L-tryptophan
N-Acetyl-L-tryptophan has the following property datas: (1)Melting point: 186°C; (2)Index of Refraction: 1.645; (3)Molar Refractivity: 67.12 cm3; (4)Molar Volume: 185.1 cm3; (5)Surface Tension: 61.6 dyne/cm; (6)Density: 1.33 g/cm3; (7)Flash Point: 308.6 °C; (8)Enthalpy of Vaporization: 92.14 kJ/mol; (9)Boiling Point: 586.6 °C at 760 mmHg; (10)Vapour Pressure: 1.32E-14 mmHg at 25°C.
3. Structure Descriptors of N-Acetyl-L-tryptophan
You could convert the following datas into the molecular structure:
(1)InChI: InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1
(2)InChIKey: InChIKey=DZTHIGRZJZPRDV-LBPRGKRZSA-N
(3)Smiles: c12c(C[C@@H](NC(C)=O)C(O)=O)c[nH]c1cccc2
4. Toxicity of N-Acetyl-L-tryptophan
The toxicity datas of N-Acetyl-L-tryptophan are as below:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 3580mg/kg (3580mg/kg) | LIVER: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980. |
mouse | LD50 | oral | 10800mg/kg (10800mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980. |
rat | LD50 | intraperitoneal | 3900mg/kg (3900mg/kg) | LIVER: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980. |
rat | LD50 | oral | 15000mg/kg (15000mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980. |
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