Identification | More | [Name]
4-Amino-L-phenylalanine | [CAS]
943-80-6 | [Synonyms]
4-AMINO-L-PHENYLALANINE 4-AMINO-PHENYLALANINE H-P-AMINO-L-PHE-OH H-PHE(4-NH2)-OH H-PHE(4-NH2)-OH 2HCL H-PHE(P-NH2)-OH 2HCL L-4-AMINOPHE L-4-AMINOPHENYLALANINE L-4-AMINOPHENYLALANINE DIHYDROCHLORIDE L-P-AMINOPHENYLALANINE 2HCL P-AMINO-L-PHENYLALANINE (S)-2-AMINO-3-(4-AMINOPHENYL)PROPANOIC ACID 4-Amino-Phe-OH (2R)-2-amino-3-(4-aminophenyl)propanoic acid 4-amino-pyenylalanine L-4-NH2-Phe-OH 4-AMINO-L-PHENYLALANINE 99% 4-Amino-Phe Aminophenyalanine p-Aminophenylalanine | [Molecular Formula]
C9H12N2O2 | [MDL Number]
MFCD00069927 | [Molecular Weight]
180.2 | [MOL File]
943-80-6.mol |
Chemical Properties | Back Directory | [Melting point ]
265 °C (decomp) | [Boiling point ]
383.5±32.0 °C(Predicted) | [density ]
1.289±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Methanol (Slightly, Sonicated), Water (Slightly, Sonicated) | [form ]
Solid | [pka]
2.14±0.10(Predicted) | [color ]
Pale Beige to Beige | [Water Solubility ]
Soluble in water. | [Sensitive ]
Air Sensitive | [CAS DataBase Reference]
943-80-6(CAS DataBase Reference) |
Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
2922498590 |
Hazard Information | Back Directory | [Chemical Properties]
Off-white crystalline powder | [Uses]
It finds its application in the purification of peptide synthetases involved in pristinamycin I biosynthesis. | [Definition]
ChEBI: 4-amino-L-phenylalanine is the L-enantiomer of 4-aminophenylalanine. It is an enantiomer of a 4-amino-D-phenylalanine. It is a tautomer of a 4-amino-L-phenylalanine zwitterion. | [Synthesis]
A mixed solution of concentrated HNO3 (60%) and concentrated H2SO4 (1.4:1.1 v/v) was prepared and cooled to 10°C. A portion of the mixed solution (3.5 mL) was slowly added dropwise to a solution of L-phenylalanine (4.139 g, 25.1 mmol) in H2SO4 (98%, 12.5 mL) with stirring. The reaction mixture was kept stirred at 10 °C for 2.5 hours. Upon completion of the reaction, the pH of the reaction solution was adjusted with NH4OH to 5. The resulting light yellow precipitate was collected by filtration, washed sequentially with a small amount of water and CH3CN, and dried to give 4-nitro-L-phenylalanine as a yellow powder (4.748 g, 90% yield). 4-Nitro-L-phenylalanine (2.006 g, 9.54 mmol) was suspended in water (35 mL), 0.2 g of 5% palladium-barium sulfate catalyst was added, and the hydrogenation reaction was carried out for 3 h at room temperature. The reaction solution was filtered through a diatomaceous earth pad and the filtrate was concentrated to give a light brown residue. The residue was washed with CH3CN to give a light brown solid (1.460 g, 85% yield) which was used directly in the next step of the reaction. 4-Amino-L-phenylalanine derivative (0.060 g, 0.33 mmol) was dissolved in 6N HCl (4 mL) and aqueous sodium nitrate solution (0.030 g/0.5 mL) was slowly added at 0 °C. The reaction mixture was stirred at the same temperature for 40 min and then diluted with 6N HCl (0.25 mL). Subsequently, aqueous sodium azide solution (0.033 g/0.75 mL) was added at 0 °C. The reaction mixture was stirred at 0 °C for 5 min and then warmed up to room temperature to continue the reaction for 1 h. The reaction mixture was then concentrated and the reaction was carried out at room temperature. Upon completion of the reaction, the reaction solution was concentrated and the residue was reprecipitated by CH3CN to give a pure colorless amorphous solid (0.0435 g, 64% yield). The analytical and spectroscopic data of the product were in agreement with literature reports [10]. | [IC 50]
Human Endogenous Metabolite | [References]
[1] Letters in Drug Design and Discovery, 2015, vol. 12, # 6, p. 466 - 470 [2] Molecules, 2013, vol. 18, # 7, p. 8393 - 8401 [3] Helvetica Chimica Acta, 1957, vol. 40, p. 80,83 [4] Chemistry Letters, 1998, # 7, p. 704 - 706 [5] Chemistry Letters, 1998, # 6, p. 537 - 538 |
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