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[ CAS No. 74124-79-1 ] {[proInfo.proName]}

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Chemical Structure| 74124-79-1
Chemical Structure| 74124-79-1
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Product Citations

Product Citations

Chandra, Shambhu Deo ; Gunasekera, Shanal ; Noichl, Benjamin Philipp , et al. DOI:

Abstract: We report a streamlined synthesis of (2S,3R,4R)-4,5-dihydroxy isoleucine (DHIle), an amino acid found in α-amanitin, which appears to be critical for toxicity. This synthetic route is transition metal-free and enables the production of significant quantities of DHIle with suitable protection for use in peptide synthesis. Its incorporation into a cytotoxic amatoxin analog is reported.

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Product Details of [ 74124-79-1 ]

CAS No. :74124-79-1 MDL No. :MFCD00009767
Formula : C9H8N2O7 Boiling Point : -
Linear Structure Formula :O2C4H4NOC(O)ONC4H4O2 InChI Key :PFYXSUNOLOJMDX-UHFFFAOYSA-N
M.W : 256.17 Pubchem ID :676246
Synonyms :

Calculated chemistry of [ 74124-79-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.44
Num. rotatable bonds : 4
Num. H-bond acceptors : 7.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.33
TPSA : 110.29 ?2

Pharmacokinetics

GI absorption : High
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) : -8.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.19
Log Po/w (XLOGP3) : -1.25
Log Po/w (WLOGP) : -1.49
Log Po/w (MLOGP) : -0.58
Log Po/w (SILICOS-IT) : -1.18
Consensus Log Po/w : -0.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.38
Solubility : 108.0 mg/ml ; 0.42 mol/l
Class : Very soluble
Log S (Ali) : -0.57
Solubility : 68.9 mg/ml ; 0.269 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.24
Solubility : 444.0 mg/ml ; 1.73 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.4

Safety of [ 74124-79-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P310-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 74124-79-1 ]

* 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.

  • Downstream synthetic route of [ 74124-79-1 ]

[ 74124-79-1 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 74124-79-1 ]
  • [ 143726-85-6 ]
  • [ 936633-33-9 ]
  • 2
  • [ 74124-79-1 ]
  • [ 302348-51-2 ]
  • [ 1255209-41-6 ]
  • 3
  • [ 129488-10-4 ]
  • [ 74124-79-1 ]
  • [ 1094503-56-6 ]
  • [ 1094506-60-1 ]
  • [ 1094506-63-4 ]
YieldReaction ConditionsOperation in experiment
Into a three-necked flask equipped with a magnetic stirrer and placed under N2 is introduced tert-butyl (2S)-2-[(3,4-dichlorophenyl)(hydroxy)methyl]piperidine-1-carboxylate (1.9 g, 5.2 mmol) dissolved in acetonitrile (30 mL). N,N'-Disuccinimyl carbamate (2.05 g, 8 mmol) and triethylamine (2.19 mL, 15.6 mmol) are then added and the reaction medium is stirred for 4 hours at RT. After concentrating the reaction medium by evaporation under RP, the residue thus obtained is taken up in saturated aqueous sodium hydrogen carbonate solution and the aqueous phase is extracted with EtOAc (3.x.30 mL). The organic phase is washed with aqueous NaCl solution, dried over MgSO4 and concentrated by evaporation under RP. The residue obtained is diluted in DCM (15 mL). This solution is then added dropwise to solution, prepared beforehand and placed in a one-necked flask, of <strong>[129488-10-4]5-amino-N-tert-butoxycarbonyl-1H-indazole</strong> (1.45 g, 6.2 mmol), DCM (40 mL) and triethylamine (1.1 mL, 7.8 mmol). The reaction medium is stirred at RT overnight. 40 mL of DCM and 30 mL of saturated aqueous sodium hydrogen carbonate solution are then added. After separation of the phases by settling, the organic phase is washed with aqueous NaCl solution, dried over MgSO4, filtered and concentrated by evaporation under RP. The residue is purified by chromatography on silica gel eluted with a 3/1 cyclohexane/EtOAc mixture. tert-Butyl (2S)-2-[(S)-(3,4-dichlorophenyl)[(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)carbamoyl]oxy}methyl]piperidine-1-carboxylate (0.215 g) is thus obtained the form of a colourless lacquer and tert-butyl (2S)-2-[(R)-(3,4-dichlorophenyl)[(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)carbamoyl]oxy}methyl]piperidine-1-carboxylate (0.434 g) is obtained in the form of a white foam. (M-H)-=617.
  • 4
  • [ 129488-10-4 ]
  • [ 74124-79-1 ]
  • [ 1094503-74-8 ]
  • [ 1094506-77-0 ]
YieldReaction ConditionsOperation in experiment
Into a one-necked flask equipped with a magnetic stirrer is introduced tert-butyl (2S)-2-[3-(ethoxycarbonyl)phenyl](hydroxy)methyl}piperidine-1-carboxylate (4.7 g, 12.8 mmol) dissolved in acetonitrile (85 mL) with N,N'-disuccinimidyl carbonate (13.1 g, 51 mmol). Triethylamine (8.95 mL, 64 mmol) is then added and the reaction medium is stirred for 4 hours at a temperature in the region of 20° C. The reaction medium is concentrated to dryness and the evaporation residue is taken up in saturated aqueous sodium hydrogen carbonate solution (50 mL) and extracted with twice 40 mL of EtOAc. A persistent insoluble material is removed by filtration of the organic phases through a sinter funnel. The filtrate is dried over MgSO4, filtered and concentrated to dryness under RP to give the activated intermediate. Into a second one-necked flask equipped with a magnetic stirrer is introduced tert-butyl 5-amino-indazole-1-carboxylate (3 g, 12.8 mmol) with DCM (125 mL) and triethylamine (2.7 mL, 19.1 mmol). Into this solution is poured the activated intermediate dissolved in DCM (40 mL) over about 10 minutes. The reaction medium is stirred in the region of 20° C. for 16 hours. The medium is hydrolysed with saturated aqueous sodium hydrogen carbonate solution (80 mL), the phases are separated by settling and the aqueous phase is re-extracted with DCM (30 mL). The combined organic extracts are dried over MgSO4, filtered and concentrated to dryness under RP. The garnet-coloured oil isolated is chromatographed on 420 g of silica gel 60, particle size 15-40 mum, contained in a column 5 cm in diameter, eluting with a 7/3v/v cyclohexane/EtOAc mixture, under an excess pressure of 0.6 bar of argon. The evaporation of the fractions gives 1.53 g of tert-butyl 5-[([(2S)-1-(tert-butoxycarbonyl)piperid-2-yl][3-(ethoxycarbonyl)phenyl]methoxy}carbonyl)amino]-1H-indazole-1-carboxylate in the form of a white-coloured foam. (M-H)-=621. 1H NMR (DMSO, 400 MHz): 70percent-30percent mixture of isomers, delta (ppm) from 0.98 to 2.00 (m, 27H); 2.98 (m, 1H); 3.90 (broad m, 1H); 4.33 (q, J=7.5 Hz, 2H); 4.50 (broad m, 1H); 6.09 (d, J=10.0 Hz, 0.7H); 6.23 (broad d, J=9.0 Hz, 0.3H); 7.50 (t, J=7.5 Hz, 0.7H); 7.58 (m, 1.3H); 7.68 (broad d, J=7.5 Hz, 0.7H); 7.75 (broad d, J=7.5 Hz, 0.3H); from 7.85 to 8.00 (m, 3H); 8.04 (broad s, 0.7H); 8.08 (broad s, 0.3H); 8.32 (s, 0.7H); 8.34 (s, 0.3H); 9.82 (broad m, 0.3H); 10.1 (s, 0.7H).
  • 5
  • [ 4138-26-5 ]
  • [ 74124-79-1 ]
  • N-(3-(1H-imidazol-1-yl)propyl)-2-((4-fluorobenzyl)amino)-1,3-thiazole-5-carboxamide [ No CAS ]
  • N1-(4-fluorobenzyl)-N1-(5-[3-(1H-imidazol-1-yl)propyl]carbamoyl}-1,3-thiazol-2-yl)piperidine-1,3-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Example 6B (0.018 g, 0.05 mmol) was dissolved in acetonitrile (0.5 ml), and treated with potassium carbonate (0.021 g, 0.15 mmol) and 1 -(2-chloroethyl)pyrrolidine (0.017 g, 0.1 mmol). The reaction mixture was heated via microwave at 180 °C for 30 minutes, concentrated in vacuo, and submitted to reverse-phase HPLC (as described in Example 6C) to provide the title compound.
  • 6
  • [ 747412-49-3 ]
  • [ 74124-79-1 ]
  • N-ε-4-methyltrityl-L-lysine [ No CAS ]
  • [ 75286-49-6 ]
  • [ 60-24-2 ]
  • 5-carboxy-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate [ No CAS ]
  • C108H153N23O19S2 [ No CAS ]
  • C108H153N23O19S2 [ No CAS ]
  • 7
  • [ 747412-49-3 ]
  • [ 74124-79-1 ]
  • C84H130N15O15PolS3 [ No CAS ]
  • [ 75286-49-6 ]
  • [ 60-24-2 ]
  • C77H121N19O14S2 [ No CAS ]
  • C77H121N19O14S2 [ No CAS ]
  • 8
  • [ 74124-79-1 ]
  • 6-(4-aminophenyl)-2-cyclopentyl-5-methyl-4,5-dihydropyridazin-3(2H)-one [ No CAS ]
  • [ 6000-50-6 ]
  • N-[4-(1-cyclopentyl-4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% To a solution of Intermediate 9, 60 mg (0.22 minol), and 4-dimethylaminopyridine, 32 mg (0.26 minol), in tetrahydrofuran, 25 mL, was added N,N-disuccinimidyl carbonate, 67.9 mg, (0.26 minol). The reaction was stirred for 1 hour then triethylamine, 0.092 mL (0.66 minol), and 2,3-dihydro-IH-pyrrolo[3,4-c]pyridine hydrochloride (6000-50-6), 41.3 mg (0.26 minol), was added and the reaction was left to stir at room temperature for 18 hours. Water was added and the mixture was extracted with dichloromethane. The combined organics were dried over solid sodium sulfate and concentrated under vacuum. Purification by flash chromatography on silica gel 60 (eluent: ethyl acetate-heptane 0:1, 1:1, 1:0 and methanol-ethyl acetate 1:9) gave thedesired product, 62.8 mg (68percent).1H NMR (300 MHz, CDCI3): 6 [ppm] = 1.16 (d, 3H), 1.57-2.00 (m, 8H), 2.46 (d, IH), 2.64 (dd, IH), 3.27 (m, IH), 4.90 (d, 4H), 5.21 (m, IH), 6.40 (s, IH), 7.30 (d, IH), 7.52 (d, 2H), 7.76 (d, 2H), 8.58 (d, IH), 8.63 (s, IH).UPLC-MS (Method 4): R 1.93 min., 100percent. MS (ESIpos): mz[M+H]418.
  • 9
  • [ 74124-79-1 ]
  • 6-(4-aminophenyl)-5-methyl-2-(2,2,2-trifluoroethyl)-4,5-dihydropyridazin-3(2H)-one [ No CAS ]
  • [ 6000-50-6 ]
  • N-{4-[4-methyl-6-oxo-1-(2,2,2-trifluoroethyl)-1,4,5,6-tetrahydropyridazin-3-yl]phenyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% A solution of 100mg of Intermediate 11(0.35 minol, 1.00 eq) in DMF (10 mL) was treated with108 mg of N,N?-disuccinimidyl carbonate (0.42 minol, 1.20 eq) and 51.4 mg of 4-dimethylaminopyridine (0.42 minol, 1.20 eq) and was left over night at room temperature. Asuspension of 81 .2 mg of 2,3-dihydro-1 H-pyrrolo[3,4-c]pyridine dihydrochloride (0.42 minol, 1 .20eq) and 667 pL of triethylamine (4.78 minol, 3.60 eq) in DMF (5 mL) was added. The reactionmixture was left for 3 days at room temperature. The mixture was poured into water. The aqueous phase was three times extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2504 and the solved was removed under reduced pressure. The residue was purified by preparative reverse phase HPLC to yield the desired productExample 11(30 mg, 20percent).1H-NMR (400MHz, DMSO-d6): oe [ppm] = 1.09 (d, 3H), 2.40-2.47 (m, IH), 2.79-2.87 (m, IH),3.42-3.54 (m, IH), 4.26-4.38 (m, IH), 4.37-4.37 (m, IH), 4.80-4.83 (m, 4H), 7.41 -7.47 (m, I H), 7.65 - 7.72 (m, 2H), 7.72 - 7.79 (m, 2H), 8.50 (d, I H), 8.61 (s, I H), 8.66 (s, I H).U PLC-MS (Method 2): R= 0.81 min; MS (ESipos): mz [M÷H] 432.
  • 10
  • [ 74124-79-1 ]
  • 6-(4-aminophenyl)-5-methyl-2-(tetrahydro-2H-pyran-4-yl)-4,5-dihydropyridazin-3(2H)-one [ No CAS ]
  • [ 6000-50-6 ]
  • N-{4-[4-methyl-6-oxo-1-(tetrahydro-2H-pyran-4-yl)-1,4,5,6-tetrahydropyridazin-3-yl]phenyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% A solution of 177 mg of Intermediate 14 (0.31 minol, 50percent purity 1.00 eq) in DMF (19 mL) wastreated with 94.7 mg of N,N?-disuccinimidyl carbonate (0.37 minol, 1.20 eq) and 45.2 mg, of 4-dimethylaminopyridine (0.37 minol, 1.20 eq). The mixture was left over night at room temperature. A suspension of 71.4 mg of 2,3-dihydro-IH-pyrrolo[3,4-c]pyridine dihydrochloride (0.37 minol, 1.20 eq) and 155 pL of triethylamine (1.11 minol, 3.60 eq) on DMF (3 mL) wasadded. The reaction mixture was stirred 3 days at room temperature. The mixture was poured into water and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over Na2SO4. The aqueous and the organic phase were evaporated under reduced pressure. Both residues were purified by preparative HPLC to yield in total 15.0mg of the desired product Example 21(0.03 minol, 11percent).1H-NMR (400MHz, DMSO-d6): oe [ppm]= 1.05 (d, 3H), 1.49- 1.61 (m, 2H), 1.80- 1.93 (m, IH),2.02 - 2.16 (m, I H), 2.29 - 2.37 (m, I H), 2.68 - 2.76 (m, I H), 3.88 - 3.99 (m, 2H), 4.70 - 4.80 (m,IH), 4.91 (d, 4H), 7.64 - 7.71 (m, 3H), 7.74 - 7.79 (m, 2H), 8.64 (d, IH), 8.72 (s, IH), 8.76 (s,I H). Three protons are not visible.U PLC-MS (Method 2): R 0.71 min; MS (ESIpos): mz [M÷H] 434.
  • 11
  • [ 74124-79-1 ]
  • 6-(4-aminophenyl)-5-methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one [ No CAS ]
  • [ 6000-50-6 ]
  • N-[4-(4-methyl-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridazin-3-yl)phenyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% A solution of 100 mg of Intermediate 23(0.36 minol, 1.00 eq) in DMF (11 mL) was treated with110 mg of N,N?-disuccinimidyl carbonate (0.43 minol, 1.20 eq) and 53.4 mg of 4-dimethylaminopyrdine (0.44 minol, 1.20 eq). The mixture was stirred over night at roomtemperature. A solution of 82.9 mg of 2,3-dihydro-1 H-pyrrolo[3,4-c]pyridine dihydrochloride (0.43minol, 1 .20 eq) and 2.99 mL of triethylamine (21.47 minol, 30 eq) in DMF (2 mL) was added. The mixture was stirred over night. THE was removed from under reduced pressure. The remaining solution was poured into water. The solid was removed by filtration, the filtrate was taken to dryness and the residue was purified by preparative reverse phase HPLC to yield 35.0mg of the desired product (21percent).1H-NMR (400MHz, DMSO-d6): oe [ppm] = 1.07 (d, 3H), 2.17 (s, 6H), 2.22-2.36 (m, IH), 2.40-2.48 (m, 2H), 2.64 - 2.70 (m, I H), 3.37 - 3.44 (m, I H), 3.59 - 3.75 (m, I H), 3.91 - 4.08 (m, I H),4.83 (d, 4H), 7.44 (d, IH), 7.63 - 7.71 (m, 2H), 7.71 - 7.79 (m, 2H), 8.50 (d, IH), 8.65 (s, IH),8.61 (s, IH).UPLC-MS (Method 1): R0.83 min; MS (ESIpos): mz[M+H]426.
  • 12
  • [ 747412-49-3 ]
  • [ 74124-79-1 ]
  • C110H159N18O16PolS3 [ No CAS ]
  • [ 75286-49-6 ]
  • [ 60-24-2 ]
  • 5-carboxy-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate [ No CAS ]
  • C108H153N23O19S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25 pmol of NH2-Fx-r-Fx-r-Fx-r-K(Mtt) on resin was reacted with S-trityl-2- mercaptoproprionic acid (4 eq), PyBOP (4 eq), and DIPEA (8 eq) in 1 mL DMF. The peptide was washed (2 x DMF/MeOH/DCM) and deprotected with trifluoroacetic (0146) acid:triisopropylsilane:DCM (5:3:92, 2 x 15 minutes). The peptide washed and equilibrated in acetonitrile:water (5: 1 ). Cysteamine (20 eq) was dissolved in 1 mL acetonitrile:water (5: 1 ) and added to the reaction mixture followed by iodine (10 eq). The reaction was stirred for 30 minutes. The peptide was washed (2 x DMF:MeOH:DCM) and reacted with 5- Carboxytetramethylrhodamine (2 eq), HBTU (2 eq), and DIPEA (4 eq) in 0.5 mL DMF for 2 hours. The peptide was washed, cleaved from resin using trifluoroacetic (0147) acid:triisopropylsilane:water (95:2.5:2.5) and precipitated in ether at -20°C for 1 hour. The precipitate was purified by HPLC and lyophilized. 5-(2,4-Dihydroxy-5-isopropylphenyl)-N-ethyl- 4-(4-(morpholinomethyl)phenyl)isoxazole-3-carboxamide (Luminespib, 3 eq, Adooq Bioscience, Irvine CA) was reacted with Nu,Nu'-Disuccinimidyl carbonate (3 eq, Sigma-Aldrich) and 4- (Dimethylamino)pyridine (12 eq, Sigma-Aldrich) in 0.4 mL DMF for 1 hour. The peptide was dissolved in 0.1 mL DMF and added to the reaction mixture and the solution was left stirring overnight. The peptide was precipitated in ether and purified by HPLC. The earlier eluting isomer was purified and tested due to its higher relative abundance. The solution was frozen in dry ice as the compound eluted from the column and lyophilized. The peptide was identified by ESI mass spectrometry, expected m/z = 2140.12, found m/z = 2140.12. The peptide was quantified using the 5-Carboxytetramethylrhodamine absorbance at 547 nm with an extinction coefficient of 92000 M"1cm"1.
  • 13
  • [ 747412-49-3 ]
  • [ 74124-79-1 ]
  • C84H131N16O15PolS3 [ No CAS ]
  • [ 75286-49-6 ]
  • [ 60-24-2 ]
  • C77H121N19O14S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25 muetaetaomicronIota of NH2-Fx-r-Fx-r-Fx-r on resin was reacted with S-trityl-2- mercaptoproprionic acid (4 eq), PyBOP (4 eq), and DIPEA (8 eq) in 1 mL DMF. The peptide was washed (2 x DMF/MeOH/DCM), cleaved from resin using trifluoroacetic (0139) acid:triisopropylsilane:water (95:2.5:2.5) and precipitated in ether at -20°C for 1 hour. The precipitate was purified by RP-HPLC, dried under vacuum and dissolved in 0.5 mL (0140) acetonitrile:water (5:1). 2-mercpatoethanol (20 eq, Sigma-Aldrich) was added to the reaction mixture followed by iodine (10 eq) and the reaction was stirred for 30 minutes. The peptide was purified by HPLC and lyophilized. 5-(2,4-Dihydroxy-5-isopropylphenyl)-N-ethyl-4-(4- (morpholinomethyl)phenyl)isoxazole-3-carboxamide (Luminespib, 3 eq, Adooq Bioscience, Irvine CA) was reacted with Nu,Nu'-Disuccinimidyl carbonate (3 eq, Sigma-Aldrich) and 4- (Dimethylamino)pyridine (12 eq, Sigma-Aldrich) in 0.4 mL DMF for 1 hour. The peptide was dissolved in 0.1 mL DMF and added to the reaction mixture and the solution was left stirring overnight. The peptide was precipitated in ether and purified by HPLC. Two isomers were identified during HPLC purification, likely due to attachment to either of the two resorcinol hydroxyls. The earlier eluting isomer was purified and tested due to its higher relative abundance. The solution was frozen in dry ice as the compound eluted from the column and lyophilized. The peptide was identified by ESI mass spectrometry, expected m/z = 1599.88, found m/z = 1599.88. The peptide was quantified via absorbance spectrophotometry using a SpectraMax M5 spectrophotometer. The absorbance profile of Compound 5 was found to be shifted as compared to Luminespib itself, therefore the peptide was quantified by cleavage in 25 mM TCEP in PBS pH 7.4 for 10 minutes, then measuring free Luminespib absorbance at 305 nm with an extinction coefficient of 8520 M"1cm"1. TCEP was not found to affect the extinction coefficient of Luminespib.
  • 14
  • [ 74124-79-1 ]
  • [ 35661-51-9 ]
  • C20H17N3O6 [ No CAS ]
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