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CAS No. : | 70-18-8 | MDL No. : | MFCD00065939 |
Formula : | C10H17N3O6S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RWSXRVCMGQZWBV-WDSKDSINSA-N |
M.W : | 307.32 | Pubchem ID : | 124886 |
Synonyms : |
GSH;γ-L-Glutamyl-L-cysteinyl-glycine;Tathion;Glutathion;Isethion;Glutathione
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 5.0 |
Molar Refractivity : | 70.37 |
TPSA : | 197.62 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -11.37 cm/s |
Log Po/w (iLOGP) : | 0.32 |
Log Po/w (XLOGP3) : | -4.5 |
Log Po/w (WLOGP) : | -2.21 |
Log Po/w (MLOGP) : | -4.04 |
Log Po/w (SILICOS-IT) : | -1.37 |
Consensus Log Po/w : | -2.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 2.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.11 |
Log S (ESOL) : | 1.82 |
Solubility : | 20100.0 mg/ml ; 65.4 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.97 |
Solubility : | 2860.0 mg/ml ; 9.3 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.08 |
Solubility : | 254.0 mg/ml ; 0.826 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 | 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 |
---|---|---|
1.99 kg | With sulfuric acid; zinc; In water; at 20℃; for 21.5h;pH 4;Electrochemical reaction; Industrial scale; Large scale; | Sodium hydroxide was added to an aqueous oxidized glutathione solution to allow pH to be adjusted to 4.0, whereby aqueous oxidized 7 glutathione solution was prepared. Powder 9 zinc was added to 160 mg/L, whereby 200 g/L aqueous oxidized 7 glutathione solution was prepared. As the electrolytic cell, anode cell (15 L) and cathode cell (15 L) were used, and the both were separated by a cation exchange membrane SELEMION CMT (manufactured by Asahi Glass Company) with an effective membrane area of 1.8 dm2. Iridium oxide-coated titanium was used as the anode, and galvanized stainless steel (SUS316) was used as the cathode. The distance between the electrode and the cation exchange membrane was set to 1.9 mm, and the circulation flow was set to 240 L/h. The anode cell contained 0.50 mol/L sulfuric acid solution (10 L), and the cathode cell contained the aqueous oxidized glutathione solution (200 g/L, 10 L) prepared above. |
With tris-(2-carboxyethyl)-phosphine hydrochloride; In aq. buffer; at 20℃;pH 8.2; | In a 0.5 mL Eppendorf Safe-Lock microcentrifuge tube, a 50.0 mM solution of oxidized glutathione (85)in 100 mM Tris buffer pH 8.2 (10.0 muL, 0.50 mumol) was diluted with Tris buffer (100 mM, pH 8.2, 470 muL).The resulting solution was vortexed few seconds and a solution of TCEP reagent in 100 mM Tris bufferpH 8.2 (10.0 muL, 0.75/2.50/5.00 mumol, respectively 1.50/5.00/10.0 equiv.) was added in one portion. Theresulting mixture was vortexed few seconds to ensure proper reagent mixing and left on the bench atroom temperature for 10 or 60 minutes. Then, a 300 mM solution of N3-EBX reagent (1a) in DMSO (10.0muL, 3.00 mumol, 6.00 equiv.) was added. The resulting mixture was vortexed few seconds to ensureproper reagent mixing and left on the bench at room temperature for 5 minutes to afford 3a. No effortwas made to exclude oxygen. The reaction was analyzed by HPLC-MS and the yield was determinedby comparing the integration area of absorption peak at 214 nm of the product in the mixture to that ofa standard curve. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Cumene hydroperoxide; C20H28N2O2Se2; In aq. phosphate buffer; at 23℃;pH 7.5;Inert atmosphere; | The GPx-like activity was followed spectrophotometrically. The test mixture contained GSH (2.0 mM), EDTA (1 mM), glutathione disulfide reductase (1.7 units/ml), and NADPH (0.4 mM) in 0.1 M potassium phosphate buffer of pH 7.5. GPx samples (80 muM) were added to the test mixture at 23 C temperature and the reaction was started by the addition of peroxide (1.6 mM). The initial reduction rates were calculated from the rate of NADPH oxidation at 340 nm in GSH assay. Each initial rate was measured at least three times and calculated from the first 5-10% of the reaction by using 6.22 mM-1 cm-1 as the molar extinction coefficient for NADPH. For the peroxidase activity, the rates were corrected for background reaction between peroxide and thiol. | |
With dihydrogen peroxide; In methanol; water; for 5h; | General procedure: Peptide 9 was formed upon oxidation of peptide CGAILR (CPC Scientific, Sunnyvale, CA, USA) by adding 10 muL of 1 % hydrogen peroxide to 1 mL of 10 muM peptide in 50/50 MeOH/H2O solution, and stirring for 5 h. Peptide 10, oxidized glutathione, was bought from Sigma-Aldrich (St. Louis, MO). | |
With C56H68Cl2NO2Ru2S3(1+)*BF4(1-); In [D3]acetonitrile; water-d2; for 24h; | To evaluate the catalytic performance of the complexes forthe oxidation of the reduced form of GSH to the disulfideform (GSSG), [10]BF4 (1 mg) was dissolved in 0.3 mL of D2O and 0.3 mL of CD3CN, and 100 equiv. of GSH(24.7 mg) were added to the solution. The sample wassubsequently analyzed by 1H NMR spectroscopy. The 1HNMR spectra were recorded immediately after samplepreparation, and then every 30 min over the period of 24 h. |
With vanadium pentaoxide; dihydrogen peroxide; In aq. phosphate buffer; at 25℃;pH 7.4;Catalytic behavior; Kinetics; | General procedure: GPx-like activity of the synthesized V2O5 and MoO3 nanowires (VNw and MNw) was followed spectrophotometrically by using the standard GR-coupled GPx assay (Fig. 1 ) [11]. (0008) The rate of the reaction was quantified by following the decrease in the absorbance of NADPH at 340nm. 1ml reaction mixture consisted of catalyst (20mugmL-1), GSH (2mM), NADPH (0.2mM), GR (?1.7U) and H2O2 (200muM) in pH 7.4 phosphate buffer (100mM). All the assays along with respective controls were carried out at 25C. Using Beer-Lambert?s law, rate of decrease in the absorbance of NAPDH (epsilon=6220M-1cm-1) was converted to rate of conversion of NADPH to NADP+ which is equal to the rate of conversion of H2O2 to H2O (Eq. (1), (2)). (1) Rate=slope6220Ms-1 (2) Rate=slope6220x6010-6muMmin-1 (0009) Sigma plots were obtained by plotting V vs [S] (Eq. (3)) and kinetic parameters like substrate binding affinity (KM) and maximum reaction velocity (Vmax) were obtained from the Lineweaver-Burk plots (Eq. (4)), where V is the rate of reaction, [S] is concentration of substrate (in our case, H2O2 and GSH). (3) V=Vmax[s]KM+[s] (4) 1v=KMvmax1s+1vmax | |
With [(eta5-Cp)RhCl(2,2?-biimidazole)]PF6; In water; at 25℃; for 30h; | The reactivity towards glutathione was determined using Ellman?smethod [34-36] to measure the unreacted GSH concentrationafter incubation with the complexes. The procedureis based on the reaction of the thiol with DTNB to givethe mixed disulfide and 2-nitro-5-thiobenzoic acid whichwas quantitatively determined by the UV-Vis spectroscopyat 412 nm. Mixtures of 1.0 ml of GSH (sample concentration0.5-3.0 mM) 1 ml of 1-3 complexes (0.5 mM) and 8 mlof H2Owere incubated at 25 C in the dark for 30 h. Next2.5 ml of the reaction mixture was treated with 2.5 ml ofDTNB in a phosphate buffer (PBS, 10 mM, pH 7.4) and theabsorbance was determined. A comparison with the referenceGSH concentration/absorbance relationship allowed thedetermination of unreacted thiol concentration. The obtainedconcentrations are the average of three independent measurements.Moreover, to examined products of the reactionGSH with the compounds the ESI mass spectra of free GSH,GSH cisplatin, GSH complexes (1-3) were recorded. | |
With dihydrogen peroxide; In water; at 37℃;Kinetics; | Reactions were carried out at 37C in a thermostattedglass cell equipped with a magnetic stirrer. In thecourse of the reaction, aliquot portions (15 muL) weretaken from the reaction vessel in order to determinethe concentration of GSH by the Ellman method [42].For this purpose, an aliquot portion was added to3 mL of a sodium phosphate buffer solution (PBS,pH 7.4) containing 0.1 mM DTNB, and the concentrationof 2-nitro-5-thiobenzoic acid, which is formedby the interaction of GSH with DTNB, was determinedspectrophotometrically (lambdamax = 412 nm, epsilon =0.14 × 105 M-1 cm-1). The concentration of basicH2O2 solutions in the absence of GSH was monitoredby an iodometric method.The rate of generation of radicals (WA) was measuredby an inhibitor method based on the consumption of theacceptor A, whose concentration changes were measuredby spectrophotometry (epsilon = 0.77 × 105 M-1 cm-1 at lambdamax = 546 nm) directly in thermostatted quartz cells (1 cm) of an Ultraspec1100Pro spectrophotometer(Amersham plc, the United States).Errors in the determination of the concentrations ofreagents and the rates of reactions did not exceed 15%.The analysis of the kinetics of the interaction ofGSH with H2O2 and the computer simulation of thekinetic curves of reagent consumption were performedusing a published program [43]. | |
With bis(2,6-dicarboxypyridyl)silver(II); In aq. phosphate buffer;pH 7; | An 8.5 mM solution of Ag2,6P in phosphate bufferwas prepared and 2.25 mL was transferred to a cuvetteand the visible spectrum (400-900 nm) recorded.Aliquots (20 lL) of reduced glutathione (GSH) solution(84.3 mM) in phosphate buffer were added to thecuvette and the spectrum re-recorded after eachaddition until the band (kmax 570 nm) attributed tosilver(II) disappeared (* 120 lL).To investigate the products of the reaction usingNMR, three solutions of reduced glutathione (6.1 mgin 1 mL of D2O, 20 mmol) were treated with 8.2 mg(18.5 mmol), 16.6 mg (36 mmol) or 24.4 mg(53 mmol) of Ag2,6P respectively. The solutionswere allowed to react overnight and then filtered intoa 5 mm NMR tube. 1H NMR spectra were obtainedusing a Bruker AVANCE 3 spectrometer operating at400.12 MHz. Samples were maintained at 300 Kduring spectral acquisition. The NMR spectra werecollected using a standard pulse sequence. The freeinduction decay was generated by a 3.13 ls pulsewidth corresponding to a 30o pulse. Each data set (4 kscans; no water suppression) was collected in 32 k ofmemory. A 1 Hz line broadening function was applied An 8.5 mM solution of Ag2,6P in phosphate bufferwas prepared and 2.25 mL was transferred to a cuvetteand the visible spectrum (400-900 nm) recorded.Aliquots (20 lL) of reduced glutathione (GSH) solution(84.3 mM) in phosphate buffer were added to thecuvette and the spectrum re-recorded after eachaddition until the band (kmax 570 nm) attributed tosilver(II) disappeared (* 120 lL).To investigate the products of the reaction usingNMR, three solutions of reduced glutathione (6.1 mgin 1 mL of D2O, 20 mmol) were treated with 8.2 mg(18.5 mmol), 16.6 mg (36 mmol) or 24.4 mg(53 mmol) of Ag2,6P respectively. The solutionswere allowed to react overnight and then filtered intoa 5 mm NMR tube. 1H NMR spectra were obtainedusing a Bruker AVANCE 3 spectrometer operating at400.12 MHz. Samples were maintained at 300 Kduring spectral acquisition. The NMR spectra werecollected using a standard pulse sequence. The freeinduction decay was generated by a 3.13 ls pulsewidth corresponding to a 30o pulse. Each data set (4 kscans; no water suppression) was collected in 32 k ofmemory. A 1 Hz line broadening function was applied | |
With dihydrogen peroxide; In aq. phosphate buffer; at 37℃;pH 7.4;Kinetics; | Bidistilled deionized water and two phosphate buffer solutions,PBS and PB, were used as reaction media. Buffer PBS (pH 7.4) is an isotonic phosphate-salt buffer solution containing sodium and potassium chlorides, sodium hydrophosphate, and potassium dihydrophosphate in which the concentration of ions in the solution corresponds to the concentration in the humanblood; PB is a buffer mixture of KH2PO4 and Na2HPO4?12H2O with pH 7.2. The reactions of GSH with H2O2 were carried outat a physiological temperature of 37C in a temperature-maintained vessel with magnetic stirring, from which samples (9 mL) were taken during the reaction. The taken samples were diluted in 3 mL of phosphate buffer (PBS, pH 7.4) containing the Ellman reagent (0.1 mmol). The concentration of formed 2-nitro-5-thiobenzoic acid equal to GSH concentration wa sdetermined spectrophotometrically: e = 0.14?105 L mol-1 cm-1 at lmax = 412 nm.32-34 | |
With [Ir(2-phenylpiridinate)2(2-(hydroxy-1-naphthyl)imidazo-[4,5-f][1,10]phenanthroline)]Cl; oxygen; In water-d2; at 20℃; for 12h;Irradiation; | General procedure: In a septum-capped tube we added 0.5mL of a solution with the L-aminoacids or L-glutathione (10mM, 0.005mmol), the metal PC (0.01mM - 1% mol for L-Methionine (Met) and L-Cysteine (Cys), or 0.1mM - 1% mol for L-Tryptophan (Trp) and L-Glutathione (GSH)) in a mixture of DMSO-d6/D2O (1:3 v/v for Met and Trp and 1:10v/v for Cys) or in a mixture of MeOD/D2O (1:3v/v for GSH). The system was purged with O2 until atmosphere saturation and irradiated with Blue LED light (lambda=460nm), 24W at room temperature during 12h. The conversion values have been calculated by 1H NMR and ESI(+) MS AR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.02 g; 0.08 g | In aq. phosphate buffer; at 90℃; for 0.0833333h;pH 6.5; | GSH (0.460 g, 1.5 mmol) and (E,E)-2,4-decadienal (0.228 g,1.5 mmol) were first dissolved in 5 mL of phosphate buffer (0.2 M,pH 6.5) in a 15-mL pressure-resistant tube, and then heated at 90 C for5 min. The resulted reaction mixture was separated on a column(3.0 cm × 60 cm) packed with polyamide resin (125-150 mum)(Mitsubishi Chemical Corporation, Tokyo, Japan) using the above automatic liquid chromatographic system with UV monitoring at 220 nm.The reaction mixture was entirely loaded on the column. The columnwas first washed with 300 mL of water, and then eluted gradually with500 mL of ammonium hydroxide (0.3 M). The target fractions werefreeze-dried and collected, yielding 0.02 g of product N4 and 0.08 g ofproduct N5, respectively. Similarly, the products N4 and N5 weresubjected to HPLC-ELSD, HPLC-MS, and1H NMR and13C NMR analyses. |
Tags: 70-18-8 synthesis path| 70-18-8 SDS| 70-18-8 COA| 70-18-8 purity| 70-18-8 application| 70-18-8 NMR| 70-18-8 COA| 70-18-8 structure
A1529482[ 815610-65-2 ]
N5-((R)-1-(((Carboxy-13C)methyl-13C)amino-15N)-3-mercapto-1-oxopropan-2-yl)-L-glutamine
Reason: Stable Isotope
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H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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