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CAS No. : | 154-92-7 | MDL No. : | MFCD00001763 |
Formula : | C13H18N4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RSYYQCDERUOEFI-JTQLQIEISA-N |
M.W : | 278.31 | Pubchem ID : | 97369 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
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With acetic anhydride; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
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With methanol at 170℃; |
Yield | Reaction Conditions | Operation in experiment |
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47% | With sodium carbonate In water at 0 - 20℃; for 0.4h; | Method A (3a, 3c, 3e-3g) General procedure: To a solution of the corresponding carboxylic acid in toluene (volume to make a 0.5 M solutionof substrate), SOCl2 (5 equiv.) was slowly added and the reaction was stirred at reflux temperaturefor 1 h. Then, volatiles were removed under reduced pressure to afford the desired acyl chloride.To a round-bottom flask charged with a solution of L-Arginine in water (volume to make a 0.2 Msolution of substrate) Na2CO3 (2equiv.) was added. The solution was cooled at 0 °C and the acylchloride (1.2 equiv.) was added portion wise. The reaction mixture was stirred at 0 °C for 10 min andthen at r.t. until complete consumption of the starting material (24 to 72 h). After that, the mixturewas acidified with a solution of HCl 3 M to pH 1, and the aqueous phase was washed 3× with DMC.The resulting aqueous phase was then basified with NaOH 4 M to pH 8, evaporated until drynessand purified by using RP18 column chromatography. The collected fractions were analyzed byUV-Vis and were then combined according to the obtained UV-spectra to afford the desired product. |
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
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With water at 20℃; pH 8; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
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With borate buffer In 1,4-dioxane for 2h; Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
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With water In N,N-dimethyl-formamide at 35℃; pH 5.0; influence of enzyme papain; influence of BzPheal=Ala; | ||
With Cudrania protease In dimethyl sulfoxide at 25℃; | ||
With trypsin aq. buffer; Enzymatic reaction; |
With water; trypsin In dimethyl sulfoxide for 0.333333h; Enzymatic reaction; | ||
With 1H-imidazole; hydrogenchloride; ethylenediaminetetraacetic acid; papain-Cys25–SH from papaya latex at 25℃; Inert atmosphere; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With water at 30℃; Peptidamidase aus dem Flavedo von Orangen; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
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With subtilisin BPN' In methanol; water kcat and Km; other cosolvents; pH 8.0; |
Yield | Reaction Conditions | Operation in experiment |
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With ethylenediaminetetraacetic acid; water; mercaptoacetic acid In dimethyl sulfoxide papain-cat. hydrolysis (spec. activity); phosphate buffer (pH=8.5); | ||
With sodium chloride; calcium chloride at 25℃; | ||
With trypsin at 27℃; |
With spermidine trihydrochloride; bovine pancreatic trypsin In aq. buffer at 36.84℃; Enzymatic reaction; | ||
With water; trypsin In aq. buffer Heating; Enzymatic reaction; | 2.1.1. Trypsin catalyzed hydrolysis of BAEE The trypsin solution (10 nM) and buffer were equilibrated at 37 °C for 200 s. Then ten aliquots of 3 μL of the 1.5mM BAEE, BA solution or the buffer were injected (see Fig. 1, Fig. 2A, S2 and S3A) or two aliquots of 15 μL of the 1.5mM BAEE solution (Fig. 2B, and S3B). The experiments were performed in buffer solutions without the crowders or crowded by 300 g/L of EG, PEG600 or PEG6000. The change in the thermal power was monitored until the signal returned to the original base line. Data analysis is presented in Fig. 2 and S3 and in Tables 1 and 2. |
Yield | Reaction Conditions | Operation in experiment |
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73% | In tetrahydrofuran; water for 4h; Ambient temperature; | |
73% | With water In tetrahydrofuran for 4h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; borate buffer; sodium chloride; calcium chloride In water at 30℃; var. of substrate, amino acid amide, conc.; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With clostripain; sodium chloride; calcium chloride In acetate buffer at 25℃; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 25℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: 1.) DCC / 1.) 1,4-dioxane, 15 min, 2.) 1,4-dioxane, 18 h 2: borate buffer (pH 8.5) / dioxane / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: ethanolic hydrochloric acid 2: methanol. ammonia | ||
Multi-step reaction with 2 steps 1: methanol. hydrochloric acid 2: methanol. ammonia |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 1h; | Each of Arg derivatives (Arg: Nacalai Tesque Inc., Kyoto, Japan; citrulline: Sigma, St louis, USA; NG-monomethyl-L-arginine: Wako Pure Chemical Industries, Ltd., Osaka, Japan; ADMA (NG,NG-dimethyl-L-argnine): ALEXIS Biochemicals, Lausen, Switzerland; and SDMA (NG,NG'-dimethyl-L-argnine): ALEXIS Biochemicals, Lausen, Switzerland) (10 µmol) was dissolved in 0.1 M NaHCO3 (200 µl), and Bz2O(10 µmol)/DMF(200 µl) was added to the solution. After stirring, the mixture was allowed to stand at room temperature for 1 hour. The reaction solution was diluted with water (200 µl), and then washed with ethyl acetate (500 µl) three times. The resulting aqueous solution was added with 6 M HCl (100 µl) and then washed with ethyl acetate (500 µl) four times. The resulting reaction solution was subjected to reverse-phase HPLV to purify the desired Bz-Arg derivative (1: Bz-Arg, 2: Bz-Arg (mono-methyl), 3: Bz-ADMA, 4: Bz-SDMA). After the purification, all of the Bz-Arg derivatives were obtained at yields of around 40%. Conditions for HPLCWaters M600 multi-solvent delivery systemUV: 220 nmColumn: Develosil ODS-UG-5 (4.6 x 150 mm)Temp.: 30°CSolvent: Starting from 5% acetonitrile in a 0.05% aqueous TFA solution, the concentration of acetonitrile was increased at a rate of 1%/min.The HPLC charts of the final purified products are shown in Fig. 2, wherein the reference number 1 represents a peak of Bz-Arg, 2 for a peak of Bz-Arg (mono-methyl), 3 for a peak of Bz-ADMA, and 4 for a peak of Bz-SDMA. The individual compounds were identified by MALDI-TOF MS (mass spectrometry). Apparatus: Applied Biosystems Voyager System 6178 [Table 1] Atoms Accurate mass number C 12 H 1.00783 N 14.0031 O 15.9949 MALDI-TOF Mass Accurate mass number (M) Calculated M+H Found M+H Bz-Arg -278.1 279.1 279.5 Bz-Arg (mono-methyl) 292.2 293.2 293.6 Bz-ADMA 306.2 307.2 307.6 Bz-SDMA 306.2 307.2 307.6 Bz-citrulline 279.1 280.1 280.3 |
Yield | Reaction Conditions | Operation in experiment |
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With polymer-supported Thermococcus litoralis L-aminoacylase at 20℃; aq. buffer; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With ethylenediaminetetraacetic acid; L-Cysteine; papain from Carica papaya latex; In aq. phosphate buffer; at 37℃; for 0.5h;pH 7.0;Enzymatic reaction; | Bz-Arg-OH standard was obtained by hydrolysis of Bz-Arg-OEt (30 mM in 0.1 M phosphate buffer pH 7.0 containing 5 mM EDTA and 5 mM cysteine) with papain (5 mg) after 30 min incubation (37 C). Reaction was stopped by precipitation of papain with MeOH, and the precipitated protein was eliminated by centrifugation (10 min at 9000×g). The supernatant containing Bz-Arg-OH was evaporated and the remaining solid was redissolved in MeOH for further analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.62% | With papain adsorbed onto polyamide; In water; acetonitrile; at 37℃; for 72.0h;Inert atmosphere; Enzymatic reaction; | Bz-Arg-OEt·HCl (0.02 mmol) and dodecylamine (0.03 mmol) were dissolved in anhydrous acetonitrile (1 ml) containing 0.25 % v/v water. Papain adsorbed onto polyamide (100 mg) was added as biocatalyst. Reactions were carried out under nitrogen atmosphere at 37 C in closed flasks vessels placed on an orbital shaker (150 rpm) for 72 h. They were stopped by addition of a methanol/acetic acid (MeOH/AcOH) 4:1 mixture, followed by a thorough wash of the biocatalyst (3 × 1 ml) with the same solvent mixture (Clapset al. 1999). Solvent extraction mixture containing water instead of AcOH was also tested for extraction of Bz-Arg-NHC12 following the same procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloro-trimethyl-silane at 20℃; for 24h; | Synthesis of Nα-benzoyl-L-arginine methyl-d3 ester. Asolution of 0.4 mmol of Nα-benzoyl-L-arginine (“BA”; AlfaAesar, Ward Hill, MA, USA) in 3 mL of methanol-d4 (Cambridge Isotope Laboratories, Andover, MA, USA) was added to a 25 mL round bottom flask. Two equivalents of trimethylchlorosilane (TMSCl) were slowly added to the mixture, and the resulting solution was gently stirred at ambient temperature for 24 h. After completion of the reaction, residual methanol-d4 and TMSCl were evaporated in a concentrator (Savant Instruments, Holbrook, NY, USA).18 The ester hydrochloride product was characterized by 1Hand 13C NMR, as well as by reverse-phase high performanceliquid chromatography (HPLC; Shimadzu, Columbia, MD, USA). |
Yield | Reaction Conditions | Operation in experiment |
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With water; trypsin In aq. buffer Heating; Enzymatic reaction; | 2.1.2. Trypsin catalyzed hydrolysis of BANA The trypsin solution (25, 12.5 or 2.5 μM) and buffer were equilibrated at 37 °C for 200 s. Then seven aliquots of 5 μL of the 4mM BANA solution, buffer (Fig. 5) or two aliquots of 25 μL of the 4mM BANA solution (Fig. 2C, only the first injection is shown) were injected. The change in the thermal power was monitored until the signal returned to the original base line. Data analysis is presented in Fig. 2 and Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 1 h / Reflux 2: sodium carbonate / water / 0.4 h / 0 - 20 °C / pH 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: Nα-benzoyl-L-arginine With copper(ll) sulfate pentahydrate In water at 60℃; for 0.166667h; Stage #2: With ammonium peroxydisulfate; silver nitrate In water at 20℃; for 3h; | 3.3. General Procedure for the Preparation of Compounds 4 from Decarboxylation of Arginine Derivatives Following the adapted procedure reported by Huang et.al,[40] to a round-bottom flask charged with a solution of derivatized L-arginine in water (volume to make a 0.4 M solution of substrate) at 60 °C, CuSO4.5H2O (1 equiv.) was added, and the solution was stirred for 10 min. Then, AgNO3 (0.15equiv.) and NH4S2O8 (1.5 equiv.) were added and the reaction was stirred at r.t. for 30 min (thereaction color evolves from blue to a green solution). After complete consumption of the starting material, the reaction mixture was concentratedunder vacuum and purified by RP-18 column chromatography. The collected fractions wereanalyzed by UV-vis and combined according to the obtained UV-spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Nα-benzoyl-L-arginine With copper(ll) sulfate pentahydrate In water at 60℃; for 0.166667h; Stage #2: With ammonium peroxydisulfate; silver nitrate In water at 20℃; for 3h; | 3.3. General Procedure for the Preparation of Compounds 4 from Decarboxylation of Arginine Derivatives Following the adapted procedure reported by Huang et.al,[40] to a round-bottom flask charged with a solution of derivatized L-arginine in water (volume to make a 0.4 M solution of substrate) at 60 °C, CuSO4.5H2O (1 equiv.) was added, and the solution was stirred for 10 min. Then, AgNO3 (0.15equiv.) and NH4S2O8 (1.5 equiv.) were added and the reaction was stirred at r.t. for 30 min (thereaction color evolves from blue to a green solution). After complete consumption of the starting material, the reaction mixture was concentratedunder vacuum and purified by RP-18 column chromatography. The collected fractions wereanalyzed by UV-vis and combined according to the obtained UV-spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Nα-benzoyl-L-arginine With copper(ll) sulfate pentahydrate In water at 60℃; for 0.166667h; Stage #2: With ammonium peroxydisulfate; silver nitrate In water at 20℃; for 3h; | 3.3. General Procedure for the Preparation of Compounds 4 from Decarboxylation of Arginine Derivatives Following the adapted procedure reported by Huang et.al,[40] to a round-bottom flask charged with a solution of derivatized L-arginine in water (volume to make a 0.4 M solution of substrate) at 60 °C, CuSO4.5H2O (1 equiv.) was added, and the solution was stirred for 10 min. Then, AgNO3 (0.15equiv.) and NH4S2O8 (1.5 equiv.) were added and the reaction was stirred at r.t. for 30 min (thereaction color evolves from blue to a green solution). After complete consumption of the starting material, the reaction mixture was concentratedunder vacuum and purified by RP-18 column chromatography. The collected fractions wereanalyzed by UV-vis and combined according to the obtained UV-spectra. |
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