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CAS No. : | 71989-33-8 | MDL No. : | MFCD00037127 |
Formula : | C22H25NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | REITVGIIZHFVGU-IBGZPJMESA-N |
M.W : | 383.44 | Pubchem ID : | 2724633 |
Synonyms : |
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 9 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 105.52 |
TPSA : | 84.86 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 2.45 |
Log Po/w (XLOGP3) : | 3.52 |
Log Po/w (WLOGP) : | 3.79 |
Log Po/w (MLOGP) : | 2.41 |
Log Po/w (SILICOS-IT) : | 3.35 |
Consensus Log Po/w : | 3.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.16 |
Solubility : | 0.0266 mg/ml ; 0.0000695 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.99 |
Solubility : | 0.00396 mg/ml ; 0.0000103 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.82 |
Solubility : | 0.000587 mg/ml ; 0.00000153 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 4.25 |
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 |
---|---|---|
General procedure: A solution of piperidine (1 mL) in anhydrous DMF (2 mL) and DCM (2 mL) was added to the peptide vessel containing the swelled resin (0.1 mmol). The mixture was allowed to rock for 30 minutes at room temperature. The solution was drained, and the resin was rinsed with DMF (3 mL x 2). A solution of 1:1 DCM/DMF (3 mL x 2) was added to the resin and the peptide vessel was allowed to rock for 3 minutes. The solution was drained, and DMF (3 mL) was added. The vessel was rocked for 3 minutes, and the solvent was drained. General procedure for peptide synthesis:1 Fmoc-amino acid (0.5 mmol), HOBT (0.068 g, 0.5 mmol), and HBTU (0.190 g, 0.5 mmol) were dissolved in anhydrous DMF (3 mL) and DCM (1 mL). DIEA (0.087 mL, 0.5 mmol) was added and the resulting solution was added to the peptide vessel containing the resin (0.1 mmol). The vessel was allowed to rock for 3 hours at room temperature, the solution was drained, and the resin was rinsed with DMF (3 mL x 2). A solution of 1:1 DCM/DMF (3 mL x 2) was added to the resin and the peptide vessel was allowed to rock for 3 minutes. The solution was drained, and DMF (3 mL) was added. The vessel was rocked for 3 minutes, and the solvent was drained. The resin 5 (0.05 mmol) was suspended in anhydrous DCM (3 mL) in a peptide vessel. Pd(PPh3)4 (0.046 g, 0.04 mmol) and phenylsilane (0.12 mL, 1.0 mmol) were added. The vessel was allowed to rock for 2 hours, and the solution was drained under vacuum. The resin was rinsed with DCM (3 mL x 2), followed by washing the resin with DCM (3 mL x 2) by rocking for 3 minutes. Generation of the side chain primary amine to generate resin-bound peptide 6 was confirmed by orange resin coloration upon testing with TNBS. Sodium azide (39 mg, 0.6 mmol) was dissolved in water (1 mL). Toluene (1 mL) was added and the solution was cooled to 0°C. Trifluoromethanesulfonic anhydride (Tf2O, 0.05 mL, 0.3 mmol) was added dropwise to the solution. The reaction mixture was stirred at 0°C for 30 minutes, followed by warming to room temperature and was stirred for 4 hours at room temperature. A saturated sodium carbonate solution was added until the reaction mixture became basic, and the organic layer was separated. The aqueous layer was extracted with toluene (2 mL x 3) and organic layers were combined. To the combined organic layers were added triethyl amine (0.02 mL, 0.15 mmol) and methanol (2 mL). The solution was transferred to the fritted vessel containing resin charged with peptide 6 (0.1 mmol). Solid zinc chloride (2.7 mg, 0.02 mmol) was then added and the mixture was rocked for 12 hours. The peptide was rinsed with DCM/DMF (1:1, 5 mL x 3) and solvent was drained under vacuum. The conversion of amine 6 to azide 7 was confirmed by the negativeTNBS test result, with the resin exhibiting a pale gray color. CuI (0.248 g, 1.3 mmol), ascorbic acid (0.228 g, 1.3 mmol) and DIEA (0.3 mL, 1.7 mmol) were dissolved in DMF (2.5 mL) and pyridine (1.5 mL). The solution was poured into the peptide vessel containing resin charged with azide peptide 7 (0.1 mmol). The appropriate substituted alkyne (0.3 mmol) was dissolved in DMF (1 mL) and transferred to the peptide vessel. Thepeptide vessel was rocked for 12 hours at room temperature. The obtained resin-bound crude products were rinsed with DMF (5 mL x 2), DMF/DCM (5 mL x 2), and DMF (5 mL) for 3 minutes for each rinse, with solvent drained under vacuum after each rinse. The resin-bound peptide 8 (0.05 mmol) was deprotected and cleaved from the resin support per previously reported protocols.1 The Fmoc group was removed according to the general procedure for Fmoc-deprotection described above. Following Fmoc removal, a cleavage cocktail of TFA/H2O/TIPS/anisole (4.5 mL/0.25 mL/0.125 mL/0.125 mL) was added to the vessel, and the vessel was allowed to rock for 3 hours. The solution was collected, and the resin was rinsed with TFA (1 mL x 2) with the rinse added to the collected solution. Ice cold ether (10 mL) was added to a separatory funnel. The combined cleavage solution was poured into the funnel, followed by 5percent acetic acid in water (5 mL). The resulting organic layer was extracted with 5percent acetic acid in water (5 mL x 3). The aqueous layer and washes were combined and the remaining TFA and acetic acid were removed under reduced pressure. The triazole peptide product 8 was obtained by lyophilization, and for initial screening was dissolved in DMSO and used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Fmoc strategy based solid phase peptide synthesis procedure was employed for preparing the non-targeting control SNEHPSDK-lipopeptide 2 as depicted schematically in Scheme 2. 500 mg of H-Eys(l3oc)-2-ClTrt resin-i (M-Soc-Eysine pre-loaded 2-chioro trityl resin, 0.77-0.79 mmol/g loading) was first swelled in 10 mE DMF for 3 hand then coupled with Fmoc-Asp(O-tert-butyl) (2 equiv) using HETU (2 equiv) and DIPEA (4 equiv) in 10 mE DMF at room temperature for 1 .5 h to afford intermediate 2 (Scheme 2). The resin was washed with 10 mE DMF and the Fmoc group was removed with a solution of piperidine:DMF (1:4, v/v, 10 mE, 5 mi 2x) at room temperature. Following the same Fmoc strategy, sequential couplings of Fmoc-Ser(Otert-butyl)-OH, Fmoc-Pro-OH, Fmoc-His(Trt)-OH, FmocEcu-OH, Fmoc-Asn(Trt)-OH and l3oc-Ser(O-tert-butyl)-OH (2 equiv each) using HETU (2 equiv) and DIPEA (4 equiv) in DMF at room temperature for 1 .5 h for each amino acid afforded the resin associated octapeptide intermediate 3 (Scheme 2). The resin-bound octapeptide intermediate 3 (Scheme 2) was taken out of the reaction vessel in 10 mE DCM, washed thoroughly with DCM (5x10 mE) and dried well. The resulting dried resin bound intermediate 3 (Scheme 2) was treated with TFA:DCM (5:95, v/v, 100 mE) for 2 hat 0° C. to obtain a protected octapeptide intermediate 4 (0.37 g, 75percent yield). N, N-di-n-octadecyl-N-2-aminoeth- ylamine (0.08 g, 0.15 mmol) was then dissolved in 3 mE dry DCM and the solution was added to an ice cold reaction mixture which has been under stirring for 30 mm containing EDCI (0.043 g, 0.23 mmol), HOST (0.034 g, 0.23 mmol), DIPEA (131 pL, 0.75 mmol) and the protected octapeptide intermediate 4 (0.33 g, 0.19 mmol) in dry DCM (5 mE). The resulting solution was lefi under stirring at room temperature for 12 h. The solvent was then evaporated in the rotary evaporator at 30° C. and the residue was dried completely under high vacuum. The dried intermediate was treated with TFA:DCM:TIS (90:5:5 v/v, 2 mE) for 3 h at 0° C. and washed with TFA:DCM (1:9, v/v, 10 mE). The acid washings were concentrated to about 1 mE and 14 mE acetone was added until a white precipitate separated. Same precipitation process was repeated five times with 14 mE acetone each time and the final precipitate was washed two times with 14 mE of dietheylether each time. The precipitate upon chloride ion exchange chromatography over 5 g Amberlyst IRA-400 resin followed by purification with reversed phase HPEC afforded the pure SNEHPSDK-lipopeptide 2 as a white, solid (188 mg, 47percent yield based on octapeptide intermediate 4 shown in Scheme 2). The purified SNEHPSDK-lipopeptide 2 was characterized by the molecular ion peak in ESIMS and purity was confirmed by reversed phase analytical HPEC using two different mobile phases. ESIMS: mlz=1444 [M+1]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: 100mg 2-chlorotrityl resin (0.5mmol/g) was swollen in dry DCM for 30min and treated with the first building block (2.0equiv) and DIEA (4.0equiv) in dry DCM. After it was shook for 1h, 80muL MeOH was added to cap the unreacted resin for another 20min. The loaded resin was washed by DCM (3×2mL) and DMF (3×2mL). Fmoc deprotection was achieved by shaken with 2mL 20percent solution of piperidine in DMF for 20min. The following Fmoc- or Boc-amino acids (4.0equiv) was coupled using 32 HATU (4.0equiv) as coupling reagent and DIEA (8.0 equiv) as base. The mixture was shaken in DMF for 1h. After each Fmoc deprotection and coupling reaction, the resin was washed by DMF (3×2mL), DCM (3×2mL) and DMF (3×2mL). The loaded resin was washed by DCM (3×2mL) and then a solution of Pd(PPh3)4 (1.0equiv) and phenylsilane (25equiv) in 2mL anhydrous DCM was added. The mixture was shaken for 1h under the protection of dry argon. After Alloc deprotection was completed, the resin was washed by DMF (3×2mL), DCM (3×2mL) and DMF (3×2mL). After coupling of the last building block, the resin was washed by DCM (3 2 mL), DMF (3 2 mL) and DCM (5 2 mL). Then a cocktail of DCM/AcOH/TFE (v/v/v = 8:1:1) was added to the resinand shaken for 1.5 h. Then the resin was filtrated off and rinsedwith DCM (5 2 mL). The combined filtrates were concentrated under low pressure and azeotroped several times with DCM to remove the Acetic acid. The side-chain-protected peptides were obtained as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The synthesis of temporin-LK 1 (1) and its analogs 2?4 was performed using Fmoc protecting strategy on Rink amide resin (2 g, 0.51 mmol). Rink amide resin was first deprotected by 20percent piperidine and phenylalanine was loaded on the resin. After the loading of first amino acid, the other Fmoc-protected amino acids were incorporated in a stepwise manner by Fmoc deprotection strategy until the desired peptidyl resin was constructed. After the formation of peptidyl resin, various protecting groups and solid support were removed by using cleavage cocktail, i.e., TFA, H2O, EDT, TIS (95:2.0:2.0:1.0) (Fig. 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The Wang resin (0.3 -0.6 mmol/g, loading capacity) was loaded to peptide synthesis vessel, washed twice with 10 v of MDC, decanted the washings, added 10 v of MDC and kept for swelling for 1 h. Fmoc-Gly-OH (3.0 - 5.0 eq.) was dissolved in MDC, added minimum quantity of DMF to obtain clear solution and the mixture was transferred to reaction vessel. Added DIPC (3.0 - 6.0 eq.) followed by DMAP (0.01- 0.1 eq.) to the reaction vessel and stirred for 1.0? 3.0 h, at rt. Drained the reaction mass and washed the amino acid loaded resin twice with MDC followed by DMF. Capping of the unreacted functional sites were carried out using acetic anhydride and DIPEA. Fmoc-deprotection of the loaded amino acid was carried out by washing the resin using 15-25 percent piperidine in DMF two times for 5 and 10 min. followed by the resin was washed with 3-5*8 v 0.01? 0.1 M HOBt in DMF. The Fmoc-Arg(Pbf)-OH (2.0? 4.0 eq.), was coupled using coupling agents such as HBTU, COMU, DEPBT, and DIC, preferably DEPBT (2.0 - 4.0 eq.) and oxymapure, HOBt, preferably oxymapure (2.0? 4.0 eq.) and DIPEA, NMM, TMP, preferably DIPEA (5.0 -8.0 eq.) and MgCl2, ZnCl2, preferably MgCl2 (0.01? 0.1 eq) and DMF/NMP mixture as solvent. The reaction was performed in nitrogen atmosphere and r.t. Upon completion of coupling of the amino acid confirmed by Kaiser Test, the excess reagents were drained and washed the peptidyl resin with 3 x 10 v DMF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The Wang resin (0.3 -0.6 mmol/g, loading capacity) was loaded to peptide synthesis vessel, washed twice with 10 v of MDC, decanted the washings, added 10 v of MDC and kept for swelling for 1 h. Fmoc-Gly-OH (3.0 - 5.0 eq.) was dissolved in MDC, added minimum quantity of DMF to obtain clear solution and the mixture was transferred to reaction vessel. Added DIPC (3.0 - 6.0 eq.) followed by DMAP (0.01- 0.1 eq.) to the reaction vessel and stirred for 1.0? 3.0 h, at rt. Drained the reaction mass and washed the amino acid loaded resin twice with MDC followed by DMF. Capping of the unreacted functional sites were carried out using acetic anhydride and DIPEA. Fmoc-deprotection of the loaded amino acid was carried out by washing the resin using 15-25 percent piperidine in DMF two times for 5 and 10 min. followed by the resin was washed with 3-5*8 v 0.01? 0.1 M HOBt in DMF. The Fmoc-Arg(Pbf)-OH (2.0? 4.0 eq.), was coupled using coupling agents such as HBTU, COMU, DEPBT, and DIC, preferably DEPBT (2.0 - 4.0 eq.) and oxymapure, HOBt, preferably oxymapure (2.0? 4.0 eq.) and DIPEA, NMM, TMP, preferably DIPEA (5.0 -8.0 eq.) and MgCl2, ZnCl2, preferably MgCl2 (0.01? 0.1 eq) and DMF/NMP mixture as solvent. The reaction was performed in nitrogen atmosphere and r.t. Upon completion of coupling of the amino acid confirmed by Kaiser Test, the excess reagents were drained and washed the peptidyl resin with 3 x 10 v DMF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The peptides were produced by SPPS. Briefly, Fmoc-Leu-SASRIN resin (150 mg, 0.1 mmol) was deprotected by 20% piperidine in DMF (7 mL) to expose the primary amine. Fmoc-L-Tle-OH (177 mg, 0.5 mmol) was coupled to the resin in the presence of COMU (214 mg, 0.5 mmol) and DIEA (90 mL, 1 mmol) in DMF (5 mL). This process of deprotection and conjugation was repeated until the desired peptide was synthesized. Cleavage of the protected peptide (orthogonal protecting groups intact) from the resin was achieved by shaking the resin with 1% TFA in dry DCM (5 x 3 mL) for 2 min. The filtrates were immediately neutralized with 5% pyridine in methanol (1 mL) and evaporated to dryness. This residue was dissolved in methanol (1 mL) and the crude peptides were precipitated in cold water (30 mL). The peptides were purified by a semi-preparative Proteo C12 HPLC column with a 15 min gradient and a flow rate of 5.0 mL/min to give the desired protected peptide. |
Tags: 71989-33-8 synthesis path| 71989-33-8 SDS| 71989-33-8 COA| 71989-33-8 purity| 71989-33-8 application| 71989-33-8 NMR| 71989-33-8 COA| 71989-33-8 structure
[ 159610-93-2 ]
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methoxypropanoic acid
Similarity: 0.91
[ 82911-78-2 ]
(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate
Similarity: 0.90
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H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
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H242 | Heating may cause a fire |
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H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
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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