2-Amino-3-(3-nitrophenyl)propanoic acid

Base Information

• Chemical Name: 2-Amino-3-(3-nitrophenyl)propanoic acid
• CAS No.: 19883-74-0
• Molecular Formula: C9H10N2O4
• Molecular Weight: 210.189
• Hs Code.: 2922499990
• NSC Number: 21948
• ChEMBL ID: CHEMBL1995504
• Mol file: 19883-74-0.mol

Synonyms:2-amino-3-(3-nitrophenyl)propanoic acid;22888-56-8;3-Nitro-DL-Phenylalanine;NSC21948;3-nitrophenylalanine;DL-3-NO2-Phe-OH;MFCD01860661;MFCD04117829;NSC-21948;2-Amino-3-(3-nitrophenyl)propanoicacid;SCHEMBL44004;CHEMBL1995504;XAA88856;3-(hydroxy(oxido)amino)phenylalanine;MFCD00069003;AKOS000175276;AKOS016843178;AM83447;AS-64002;NCI60_001825;PD197212;SY035321;SY239468;CS-0156977;FT-0696020;FT-0696021;FT-0697810;EN300-1846538;A878399;3-Nitro-DL-phenylalanine (H-DL-Phe(3-NO2)-OH)

Chemical Property of 2-Amino-3-(3-nitrophenyl)propanoic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.74E-07mmHg at 25°C
• Melting Point: 256-258oC
• Refractive Index: 1.614
• Boiling Point: 410.8 °C at 760 mmHg
• PKA: 2.12±0.10(Predicted)
• Flash Point: 202.3 °C
• PSA: 109.14000
• Density: 1.408 g/cm³
• LogP: 1.77270
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO (Slightly), Water (Slightly, Sonicated)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 210.06405680
• Heavy Atom Count: 15
• Complexity: 251

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Nitro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])CC(C(=O)O)N
• Uses: L-3-Nitrophenylalanine is a derivative of L-Phenylalanine (P319415), and is used in the photocleavage of polypeptide backbones. L-Phenylalanine is an essential amino acid. L-Phenylalanine is biologically converted into L-tyrosine, another one of the DNA-encoded amino acids, which in turn is converted to L-DOPA and further converted into dopamine, norepinephrine, and epinephrine.

Technology Process of 2-Amino-3-(3-nitrophenyl)propanoic acid

There total 13 articles about 2-Amino-3-(3-nitrophenyl)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

m-Nitrocinnamic Acid (555-68-0,1772-76-5) → (2S)-2-amino-3-(3-nitrophenyl)propanoic acid (19883-74-0)

Guidance literature:

With ammonium hydroxide; borane-ammonia complex; In aq. buffer; at 37 ℃; pH=9.6; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/anie.201410670

Reference yield: 37.0%

DL-N-acetyl-3-nitrophenylalanine (170157-49-0) → (2S)-2-amino-3-(3-nitrophenyl)propanoic acid (19883-74-0)

Guidance literature:

With hydrogenchloride; sodium hydroxide; acylase I from Aspergillus melleus; In water; at 37 ℃; for 60h; pH=7.2; Enzymatic reaction;

Reference yield:

3-nitrophenylalanine (22888-56-8) → (2S)-2-amino-3-(3-nitrophenyl)propanoic acid (19883-74-0) + (2R)-2-amino-3-(3-nitrophenyl)propanoic acid

Guidance literature:

With phenylalanine ammonia-lyase from Pseudozyma antarctica yeast; In aq. buffer; at 30 ℃; for 168h; pH=8.5; Time; stereoselective reaction; Resolution of racemate;

DOI:10.1016/j.cattod.2020.04.002

upstream raw materials:

DL-N-acetyl-3-nitrophenylalanine

`Diazinon`

acrylic acid

3-nitro-aniline

Downstream raw materials:

N-(TIPPS)-3-nitro-(L)-phenylalanine

3-nitrophenylalanine

3-(3-nitro-phenyl)-2-oxo-propionic acid

N-(TIPPS)-3-nitro-(L)-phenylalanine 4-ethoxycarbonylpiperazide

Refernces

• 1、 Zhu, Longbao,Feng, Guoqiang,Ge, Fei,Song, Ping,Wang, Taotao,Liu, Yi,Tao, Yugui,Zhou, Zhemin. "One-Pot Enzymatic Synthesis of d-Arylalanines Using Phenylalanine Ammonia Lyase and l-Amino Acid Deaminase". . p. 1 - 15. Retrieved 2018/06/11.
• 2、 Rowles, Ian,Groenendaal, Bas,Binay, Baris,Malone, Kirk J.,Willies, Simon C.,Turner, Nicholas J.. "Engineering of phenylalanine ammonia lyase from Rhodotorula graminis for the enhanced synthesis of unnatural L-amino acids". . p. 7343 - 7347. Retrieved 2016/10/30.