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CAS No. : | 102410-65-1 | MDL No. : | MFCD00155632 |
Formula : | C23H19NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PCJHOCNJLMFYCV-NRFANRHFSA-N |
M.W : | 373.40 | Pubchem ID : | 7269367 |
Synonyms : |
(S)-N-Fmoc-α-phenylglycine;N-9-Fluorenylmethoxycarbonyl-L-phenylglycine;(S)-2-[[[(9H-Fluoren-9-yl)methoxy]carbonyl]amino]phenylethanoic acid;Benzeneacetic acid, α-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (S)-;Fmoc-(S)-phenylglycine
|
Chemical Name : | (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid |
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 |
---|---|---|
With 3,3-dichloro-1,2-diphenylcyclopropene; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - 20℃; for 0.166667h; | General procedure: To a solution of 3,3-dichloro-1,2-diphenylcyclopropene at -10 oC [1.1 equiv. prepared by adding diphenylcyclopropenone (1.0 equiv.) in DCM and oxalyl chloride (1.0 equiv.) at rt and stirred until the gas evolution has ceased] was added a solution of Nalpha-protected amino acid (1.0 equiv.) and diisopropylethylamine (1.2 equiv.) in dichloromethane and stirred. After 10 min hydroxylamine hydrochloride (NH2OH.HCl, 1.5 equiv.) in methanolic potassium hydroxide was added to the reaction mixture and stirred of another 45 min. The solvent was removed under reduced pressure; the residue obtained was diluted with EtOAc, washed with 10% citric acid solution, water and brine solution. The organic phase was dried over anhydrous Na2SO4 and removed under reduced pressure. The crude residue was purified by column chromatography using n-hexane and ethyl acetate as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A synthesis procedure similar to that described in Example 1 was used in making this library. A NovaSyn TGR resin for making peptide amides (substitution 0.2 mM/gm) was used. Fmoc synthetic strategy was employed using the following protected amino acids: Fmoc-Trp(Boc), Fmoc-Cys(StBu), Fmoc-Xxx, and Fmoc-His(Trityl). The Xaa amino acids were Trp, HomoPhe, 2'-Naphthylalanine, and Phenylglycine. The peptide resin Cys(StBu)-Trp-NH2 was split into four equal pools and one of the Xaa amino acids was coupled to one individual pool. After completion of the coupling reaction, the four resin pools were mixed again. The synthesis proceeded with the coupling of His followed by acetylation of the N-terminus. After the complete assembly of the peptide chain Ac-His(Trt)-Xaa-Cys(StBu)-Trp(Boc)-NH2, the StBu group was removed by treatment with DMF/tributylphosphine and rhenium-oxo metal ion was complexed as generally described above. The fully protected metallopeptide was deblocked and liberated from the solid support by treatment with a cleavage cocktail (95:5 mixture of trifluoroacetic acid-triisopropylsilane) for three hours. The metallopeptide library was recovered by precipitation using cold ether. The resulting pellet was washed twice and 0.5 ml of 95% acetic acid was added. After one-half hour 5 ml of water was added and the solution was freeze-dried yielding the desired library in solid form. Mass spectrometric analysis of the library pool confirmed the correct masses for all four members of the library: TABLE 3 Mass Calculated (M + 1) Compound Structure Mass found 1Ac-His-Phg-Cys-Trp-NH2 815.7 and 815.2 and (SEQ ID NO:6) 817.6 816.7 2Ac-His-Trp-Cys-Trp-NH2 868.8 and 868.0 and (SEQ ID NO:3) 870.7 870.1 3Ac-His-HPhe-Cys-Trp-NH2 843.8 and 842.8 and (SEQ ID NO:4) 845.7 845.2 4Ac-His-2 'Nal-Cys-Trp-NH2 880.0 and 879.1 and (SEQ ID NO:5) 881.9 880.9 As noted in TABLE 3, two molecular ion peaks differing in mass units of 2 were calculated and observed for each structure; this difference is presumptively due to the presence of two natural isotopes of rhenium, Re-185 and Re-187, in the complexation step. In addition, the ar a under the observed peaks in the spectrometric analysis showed that for each structure the area was in a 1:2 ratio, which is identical to and presumptively related to the relative abundance of Re-185 and Re-187 isotopes. These results confirmed the complexation of rhenium to the peptides. The spectral analysis is shown at FIG. 10.These results were also confirmed by HPLC analysis of this library of four compounds, which results were compared to HPLC analysis of each of the four individual members performed under identical HPLC conditions. As is evident from FIG. 11, each of the four member components are present in the library mixture. In the HPLC profile each of the metallopeptide has resolved into two isomers due to alternate orientations (syn and anti) of the rhenium oxo core. The HPLC analysis also revealed the lack of uncomplexed linear peptides in the preparation. All four compounds used for this comparison were individually prepared using methods identical to that described above for synthesis of the library. The HPLC profiles are shown as FIGS. 11A to 11E. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; diisopropyl-carbodiimide; In 1-methyl-pyrrolidin-2-one; at 20℃; | To the resin product of the previous step (0.1 mmol) was added 20% piperidine in N,N-dimethylformamide (2 mL) and the reaction mixture was shaken at ambient temperature for 30 minutes. The mixture was filtered and the resin was washed with N,N-dimethylformamide (3×5 mL), methanol (3×5 mL) and dichloromethane (3×5 mL). The resin was then suspended in N-methylpyrrolidinone (2 mL) (S)-N-<strong>[102410-65-1]Fmoc-phenylglycine</strong> (112 mg, 0.3 mmol), diisopropylcarbodiimide (47 muL, 0.3 mmol) and 1-hydroxybenzotriazole (41 mg, 0.3 mmol) were added. The resulting mixture was shaken at ambient temperature overnight and filtered. The resin was washed with N,N-dimethylformamide (3×10 mL), methanol (3×10 mL), dichloromethane (3×10 mL) and dried in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25℃; for 1h; | General procedure: Each 2-chlorotrityl chloride resin (100 mg, 1.6 mmol/g) was placed in a 5 mL polypropylene syringe fitted with a polyethylene filter disc. Each resin was washed with CH2Cl2 (2 mL, 1 h), and a solution of the corresponding Fmoc-amino acid 3a-mm (0.16 mmol) and iPr2NEt (109 muL, 0.64 mmol) in CH2Cl2 (2 mL) were then added. Each mixture was agitated for 1 h at 25 C. Solvents and soluble reagents were removed by suction. All resins were subjected to the following washing treatments with CH2Cl2-MeOH-iPr2NEt (17:2:1, 2 mL × 3), DMF (2 mL × 3), and CH2Cl2 (2 mL × 3). | |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 3h; | Example 7 N-Boc-N-methyl-L-alanine-L-cyclohexylglycineA solution of Fmoc-L-cyclohexylglycine (3.6 g, 9.6 mmol) dissolved in DCM (50 mL) and DIPEA (5.6 mL, 32 mmol) was added to 2-chlorotrityl chloride resin (5 g, 8 mmol) and gently agitated for 3 hours at room temperature. The resin was washed with DCM 4 times, DCM/MeOH/DIPEA (17:2:1) 3 times, DCM 3 times, and 2 times dimethylacetamide (DMA). The Fmoc group was removed by treating the resin with 20% piperidine/DMA (50 mL) for 15 minutes. The resin was washed with DMA 6 times. A solution of Boc-N-methylalanine (3.3 g, 16 mmol), HBTU (6.1 g, 16 mmol), and DIPEA (5.6 mL, 32 mmol) and DMA/DCM (1 :1, 50 mL) was added to the resin and gently agitated for 2 hours at room temperature. The resin was washed with DMA 5 times, DCM 2 times, and dried under reduced pressure. The dipeptide was cleaved from the resin by gentle agitation with HOAc/TFE/DCM (1 :1 :3, 100 mL) for 2 hours at room temperature. The resin was removed by filtration and the solution concentrated. Residual AcOH was removed by azeotroping with hexanes (15 times volume). The solid residue was purified by reverse-phase <n="75"/>HPLC (CiS, MeCN-H2O, 0.1%TFA) and the solvents removed by lyophylization to provide 1.2 (43%) of dipeptide N-Boc-N-methyl-L-alanine-L-cyclohexylglycine as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
BEAD LOADING Rink Amide MBHA resin (87 mg, 0.06 mmol, 0.69 mmol/g loading) was pre-swelled in a 5 mL disposable syringe equipped with a frit by rotating with DCM (3 mL) for 1 h. The resin was then washed with DMF (5 X 4 mL). The Fmoc protecting group on the bead was removed by treatment with 5 bed volumes (ca. 4 mL) of a 20% piperidine solution in DMF for 20 min. Meanwhile, Fmoc-Phe-OH (116 mg, 0.3 mmol, 5 equiv) was dissolved in DMF (3 mL) along with HOBt (41 mg, 0.3 mmol, 5 equiv). Diisopropyl carbodiimide (DIC) (50 muL, 0.3 mmol, 5 equiv) was then added and the resulting mixture was stirred at room temperature for 20 min. After 20 minutes, the resin was washed with DMF (5 X 4 mL). To the thoroughly washed resin bed, was added the coupling solution (Fmoc-Phe-OH,HOBt, and DIC), and the resulting mixture was rotated for 12 h. The loaded resin was then washed with DMF (5 X 4 mL) and used in subsequent Fmoc solid phase peptide synthesis as described below. FMOC REMOVAL The Fmoc group of the terminal amino acid of the growing peptide chain was deprotected by treating the resin beads (0.69 mmol/g loading) with a 20% solution of piperidine in DMF (ca. 4 mL) with rotation for three minutes. The deprotection cocktail was then discharged from the syringe and the resin beads were treated with a fresh portion of 20% piperidine in DMF for three minutes.This protocol is repeated until the resin beads have been treated with four aliquots of 20% piperidine in DMF. The final portion is then discharged from the syringe and the deprotected beads are washed with DMF (5 X 4 mL). The washed, deprotected resin beads were then immediately coupled with the next amino acid in the sequence. HOBT-MEDIATED COUPLING The next amino acid in a desired sequence was activated as the HOBt ester by dissolving the desired amino acid (0.3 mmol, 5 equivalents relative to the 0.69 mmol/g resin loading) along with HOBt (41 mg, 0.3 mmol, 5 equiv) in DMF/DCM (1:1) (3 mL). To the resulting solution was added DIC (50 muL, 0.3mmol, 5 equiv) and the resulting solution was stirred at room temperature for twenty minutes (usually while the terminal amino acid of the resin bound sequence is deprotected).The resulting solution of HOBt ester was added to the N-terminal deprotected, resin-bound, peptide sequence and the mixture was rotated for one hour. The resin beads were then thoroughly washed with DMF (5 X 4 mL). The resulting N-terminal, Fmoc-protected, resin-bound peptide sequence was then resubjected to the Fmoc removal protocol and subsequent HOBt couplings until the desired sequence had been assembled. N-TERMINAL O-IODOBENZOATE CAPPING The N-terminus of the peptide was capped with the o-iodoarylamido active site by the HOBt active ester methodology. The o-iodobenzoic acid (0.3 mmol, 5 equivalents relative to the 0.69 mmol/g resin loading) was dissolved along with HOBt (41 mg, 0.3 mmol, 5 equiv) in DMF/DCM (1:1) (3 mL). To the resulting solution was added DIC (50 muL, 0.3 mmol, 5 equiv) and the resulting solution was stirred at room temperature for twenty minutes (usually while the terminal aminoacid of the resin bound sequence is deprotected).The resulting solution of HOBt ester was added to the N-terminal deprotected, resin-bound, peptide sequence and the mixture was rotated for one hour. The resin beads were then thoroughly washed with DMF (5 X 4 mL). TFA CLEAVAGE/GLOBAL SIDE-CHAIN DEPROTECTION OF PEPTIDES Peptides were cleaved from the resin beads by employing the following protocol: The fully assembled, resin-bound peptides were prepared for cleavage by washing the beads with DMF (5 X 4 mL), DCM (5 X 4 mL), and methanol (5 X 4mL). The syringe plunger was removed from the barrel and the resin beads were dried overnight in the vacuum oven at 25 C. The following day, the resin was treated with a cleavage cocktail comprised of a mixture of TFA/H2O/TIS(95:2.5:2.5) (3 mL) for 2.5 h with minimal, intermittent agitation. The cleavage cocktail, containing the solvated, resin-free peptide was then ejected into a 5 mL pear-shaped flask and the solvent was removed under a stream of nitrogen to give a thick oil. The crude peptide was then precipitated by the addition of ice-cold diethyl ether. The solid peptide was then isolated by vacuum filtration and washed with copious amounts (ca. 15-20 mL) of cold ethyl ether. The solid peptide was then dried in vacuo. The identity of the desired sequence was verified by MALDI-TOF mass spectrometry. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 6h;Cooling with ice; | Example 3: Synthesis of Cyclic dipeptide: Cyclic Phenylglycinylphenylglycine [(3,6- diphenylpiperazine-2,5-dione) or cyclic (L-Phg-L-Phg)] The synthesis of cyclic dipeptide involves the following 2 steps. Step I: Synthesis of protected Dipeptide 9-Fluorenylmethoxycarbonyl (Fmoc)-L-phenylglycine (<strong>[102410-65-1]Fmoc-Phg-OH</strong>) and L- phenylglycine methyl ester (H-Phg-OMe) are prepared by using standard protection protocols. Fmoc protected L-phenylglycinylphenylglycine methylester (Fmoc-Phg-Phg- OMe) is prepared by peptide coupling procedure. <strong>[102410-65-1]Fmoc-Phg-OH</strong> (2 g, 5.16 mmol) is dissolved in dichloromethane, H-Phg-OMe (1.23 g, 5.67 mmol), l-ethyl-3-(3- dimethylaminopropyl) carbodiimide (EDC.HC1, 1.19 g, 6.19 mmol), 1- hydroxybenzotriazole and (HOBt, 1.2 g, 6.19 mmol) are added. The solution is cooled to ice temperature. Diisopropylethylamine (DIPEA, 2.14 g, 16.51 mmol) is added and the reaction mixture is stirred at ice temperature for 1 h and then at room temperature for 5 h. The reaction progress is monitored by thin layer chromatography (TLC). Reaction mixture is evaporated to dryness and extracted from dichloromethane, washed with water, dried over anhydrous sodium sulfate. The solvent is evaporated to obtain Fmoc- Phg-Phg-OMe in quantitative yield. The cyclic dipeptide Phenylglycinylphenylglycine shown in Figure 1 was prepared by coupling <strong>[102410-65-1]Fmoc-Phg-OH</strong> with Phg-OMe using peptide coupling reagents. The protected dipeptide (Fmoc-Phg-Phg-OMe) under Fmoc- deprotection conditions resulted in cyclic Phenylglycinylphenylglycine in quantitative yield, which spontaneously self-assembled to give insoluble 2D mesosheets with large lateral dimensions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of acid (1.0 mmol) and T3P (1.2 mmol) in dry CH3CN (8.0 mL) was added Et3 N (1.5 mmol) at 0 C followed by the finely ground Na2S (3.0 mmol) and the reaction mixture was stirred for 2 to 3 h till the completion of reaction as monitored by TLC. Then the reaction mixture was concentrated and then diluted with water. The resultant solution was then acidified with citric acid solution (10%) and the product was extracted into EtOAc (10 mL). The organic layer was washed with water (2 × 10 mL), brine (10 mL) and dried over anhydrous Na2SO4. Solvent was evaporated in vacuo to obtain aminothioacid in a quantitative yield.Method for HPLC analysis: Gradient 0.1% TFA, water/acetonitrile (30:70) in 30 min with a flow rate of 0.5 ml/min. lambda = 254 nm (Fmoc, Z), 211 nm (Boc). | ||
With sodium sulfide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In acetonitrile; at 0℃; | General procedure: To a soln of the appropriate carboxylic acid (1.0 mmol) and T3P (2.2 mmol) in anhyd MeCN (8.0 mL) was added Et3N (1.5 mmol)at 0 C, followed by finely ground Na2S (3.0 mmol). The resulting mixture was stirred for 2-3 h until the reaction was complete (TLC monitoring), concentrated and then diluted with H2O. The mixture was acidified with aq citric acid soln (10%) and the product was extracted with EtOAc (10 mL). The organic layer was washed with H2O (2 × 10 mL) and brine (10 mL), and then dried over anhyd Na2SO4. The solvent was evaporated in vacuo to afford the corresponding amino thioacid in quant. yield. |
Tags: 102410-65-1 synthesis path| 102410-65-1 SDS| 102410-65-1 COA| 102410-65-1 purity| 102410-65-1 application| 102410-65-1 NMR| 102410-65-1 COA| 102410-65-1 structure
[ 574739-36-9 ]
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-phenylacetic acid
Similarity: 0.95
[ 198544-94-4 ]
(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((diphenyl(p-tolyl)methyl)amino)hexanoic acid
Similarity: 0.94
[ 174879-28-8 ]
2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid
Similarity: 0.94
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H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
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 |
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