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CAS No. : | 99896-85-2 | MDL No. : | MFCD00057952 |
Formula : | C12H22N6O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IYMAXBFPHPZYIK-BQBZGAKWSA-N |
M.W : | 346.34 | Pubchem ID : | 104802 |
Synonyms : |
Arg-Gly-Asp;RGD Peptides
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
54% | Stage #1: glycyl-L-aspartic acid; Nα,NG,NG'-tri-Boc-L-arginine N-hydroxysuccinimide ester With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: With trifluoroacetic acid In chloroform |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In various solvent(s) at 4℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 19h; | 6 The molar ratios of all the conjugations were 1:1.5:1.5 for HO-PEG-NSu:peptide:DIPEA. Under anhydrous conditions, a total of 387.9 mg HO-PEG-NSu (0.18 mmol) was dissolved in 7.76 ml anhydrous DMF from the solvent system, added to 9 vials with an aliquot of 8.7 ml for each vial, followed by the addition of 9 types of peptides, 0.03 mmol for each peptide (i.e., RGD: 10.4 mg, PHSRN: 609 Da, 18.3 mg, PHSRNRGD: 938 Da, 28.1 mg, PHSRNG3RGD: 1109 Da, 33.3 mg, PHSRNG6RGD: 1281 Da, 38.4 mg, PHSRNGP4GRGD: 1441 Da, 43.2 mg, G7: 418 Da, 12.5 mg, G3RGDG: 648 Da, 17.2 mg or G3PHSRNG: 835 Da, 25.1 mg) to each vial. The solutions were stirred and purged with argon for 19 h, precipitated in cold ether and dried in a vacuum oven for overnight. The reactions were monitored by HPLC and the final products were characterized with MS-spec (Ion Spec, Fourier Transform Mass Spectrometer): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 17h; Sonographic reaction; | 6 During the reaction with RGDW and RGD described above, aggregates with a diameter of 0.10.5 mm formed in both solutions. The presence of a hydrophobic group (i.e., Ac) and a hydrophilic group (i.e., RGD or RGDW) could have facilitated the self-assembly of the molecules. To resolve the problem, sonication was introduced into the reaction system. Under anhydrous conditions, four batches of 0.221 g Ac-PEG-NSu (0.1 mmol) were dissolved in 4.42 ml anhydrous DMF, followed by the addition of 30.6 mg Trp (0.15mmol), 69 mg RGD (0.2 mmol), 80 mg RGDW (0.15 mmol) or 91.4 mg PHSRN (0.15 mmol) respectively. Containers of the four solutions were placed in a sonicator and sonication was applied 5 min every 20 min. The solutions were stirred while being purged with argon at room temperature, and monitored by HPLC up to 17 h, precipitated with cold ether, filtered and dried in a vacuum oven overnight: For the synthesis of Ac-PEG- RGD, the molar ratio of Ac-PEG-NSu:RGD:DIPEA was 1:2:2. The conversion ratio reached the highest at 77.7% after 3.5 h and decreased to 75.3% after 17 h reaction. After the product was dried, the conversion increased to 81.5%. A total of 143.6 mg product was obtained out from 220.9 mg, a yield of around 59%. However, after 17 h of reaction, the peak denoting Ac-PEG-RGD became broader. This may be due to the presence of a guanidinium group at the side chain of Arg that could compete with the N-terminal of the peptide and conjugate to the activated COOH terminal after long period of reaction time. |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; | 6 To synthesize α-acryloyl-ω-RGDW-acetate-PEG (Ac-PEG-RGDW), 88.4 mg Ac-PEG-NSu (2210 Da, 0.04 mmol) was dissolved in DMF followed by the addition of 32 mg RGDW (0.06mmol) and purged with argon. A total of 10.4 ul DIPEA (0.06 mmol) was added to the solution via a syringe. The solution was stirred and purged with argon for 1 h, precipitated in cold ether, filtered and dried in a vacuum oven overnight to obtain Ac-PEG-RGDW: Synthesis of Ac-PEG-RGD was the same as described above with exception that different amounts of reagents were used (i.e. 222 mg Ac-PEG-NSu (0.1 mmol), 52 mg RGD (0.15 mmol) and 26 ul DIPEA (0.15 mmol) )The reaction proceeded in DMF and completed after 1 h demonstrated by the disappearance of the peak at around 13.1 min for Ac-PEG-NSu and the appearance of a new peak at around 8.8 min. The new peak was associated with UV absorbance at 280 nm for Ac-PEG-RGDW and UV absorbance at 200 nm for Ac-PEG-RGD. After precipitation in cold ether and filtration, solids resulted for both reactions. However, the solids did not dissolve in acetonitrile completely. The solids were used to construct TMPTA networks but did not dissolve in TMPTA at 80° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 4-toluenesulfonic acid; H2 / Pd/C / dimethylformamide / 48 h 2.1: N-methylmorpholine / dimethylformamide / 24 h / 20 °C 2.2: 54 percent / TFA, 50 percent / CHCl3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.3 3. 3. L-Arginyl-glycyl-L-aspartic acid The protected tripeptide from the previous step (10 g) was hydrogenated at 50 psi in methanol-acetic acid-water (60:20:20, 300 ml) for 72 hours over palladium on carbon (5%, 3 g), when reaction was complete by TLC. The catalyst was filtered off, the methanol evaporated under reduced pressure and the residue lyophilized to give the tripeptide as a white powder. Yield: 3 g. The product was homogeneous by thin layer chromatography (Systems: A, isopropanol:ammonia,1:1; B, n-butanol-acetic acid:water:pyridine, 60:12:40:48). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hydrogen fluoride | 1 Preparation of RGD Cyclic Peptide After the synthesis, the resin was stirred in anhydrous hydrofluoric acid containing 5% p-cresol at 0° C. for 1 hr. The crude product was precipitated by cold ethyl ether and then purified by high-pressure preparative chromatography. The purified sample was dissolved in 0.25M phosphate buffer (pH 7.5) containing 6M GuHCl and then 2% thiophenol was added. The solution was purified and lyophilized to obtain RGD cyclic peptide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,2-dichloro-ethane In water at 37℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; 1,2-dichloro-ethane In water at 37℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 24 h / Reflux 2: deuterium / water-d2 / 36 h / 55 °C / 1500.15 Torr / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With deuterium In water-d2 at 55℃; for 36h; Inert atmosphere; enantiospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With methanol; triethylsilane; water; trifluoroacetic acid at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76 %Spectr. | With hydrogenchloride; sodium hydroxide; potassium hexacyanoferrate(III) In water; water-d2 at 20℃; for 0.333333h; | Oxidative peptide fragment ligations. General procedure: Ac-(AA1)n-SH (3.1-30.0 mM) and (AA2)m-X(X = CO2H or CN; 1-2 equiv.) were dissolved in degassed D2O and the solutionwas adjusted to pD 9.5 with NaOH. Potassium hexacyanoferrate(III) (K3[Fe(CN)6];3 equiv.) was added and the solution was stirred at room temperature for 20 min while being maintained at pD 9.5 with NaOH. The resulting suspension was centrifuged and the supernatant was analysed by one- and two-dimensional NMR spectroscopy (1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC). The ligationproduct (Ac-(AA1)n-(AA2)m-X; X = CO2H or CN) was quantified using relativeintegral analysis by 1H, 1H-13C HMBC NMR spectral analysis and HRMS. Yieldsand HRMS data are given in Table 2 and Supplementary Table 15, and characterization data are reported in Supplementary Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 35℃; for 0.5h; |
A1365768[ 2378808-45-6 ]
(S)-2-(2-((S)-2-Amino-5-guanidinopentanamido)acetamido)succinic acid trifluoroacetate
Reason: Free-salt