4-Fluoro-D-phenylalanine

Base Information

• Chemical Name: 4-Fluoro-D-phenylalanine
• CAS No.: 18125-46-7
• Molecular Formula: C9H10FNO2
• Molecular Weight: 183.182
• Hs Code.: 29224999
• European Community (EC) Number: 686-379-9
• UNII: 963G7O1PVE
• Nikkaji Number: J987C
• Wikidata: Q27271856
• ChEMBL ID: CHEMBL1434241
• Mol file: 18125-46-7.mol

Synonyms:4-Fluoro-D-phenylalanine;18125-46-7;D-4-Fluorophenylalanine;(R)-2-Amino-3-(4-fluorophenyl)propanoic acid;H-D-Phe(4-F)-OH;D-PHENYLALANINE, 4-FLUORO-;p-Fluoro-D-phenylalanine;(2R)-2-amino-3-(4-fluorophenyl)propanoic acid;4-Fluorophenylalanine, D-;R-(+)-4-Fluorophenylalanine;(R)-4-FLUOROPHENYLALANINE;UNII-963G7O1PVE;963G7O1PVE;(2R)-2-azaniumyl-3-(4-fluorophenyl)propanoate;MFCD00063063;D-4-Fluoro phenylalanine;Lopac-F-4646;SCHEMBL72793;3-(4-fluorophenyl)-l-alanine;CHEMBL1434241;XWHHYOYVRVGJJY-MRVPVSSYSA-N;AKOS016842810;AC-5834;AM83344;CS-W015995;HY-W015279;NCGC00015435-01;AS-14702;F0901;4-Fluoro-D-phenylalanine (H-D-Phe(4-F)-OH);EN300-199904;A812599;Q-101536;Q27271856;Z995228438;p-Fluoro-D-phenylalanine, >=99.0% (sum of enantiomers, HPLC)

Chemical Property of 4-Fluoro-D-phenylalanine

Chemical Property:

• Melting Point: ~245ºC
• Boiling Point: 313.3ºCat760mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 143.3ºC
• PSA: 63.32000
• Density: 1.293g/cm³
• LogP: 1.48040
• Storage Temp.: Store at RT.
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 183.06955672
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

98%, ^*data from raw suppliers

4-Fluoro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Harmful:
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)F
• Isomeric SMILES: C1=CC(=CC=C1C[C@H](C(=O)O)N)F
• Uses: 4-Fluoro-D-phenylalanine is a building block used in the preparation of new peptidomimetics.

Technology Process of 4-Fluoro-D-phenylalanine

There total 38 articles about 4-Fluoro-D-phenylalanine 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: 99.0%

4-fluoro-(RS)-phenylalaninamide hydrochloride (133919-66-1) → (R)-4-fluorophenylalanine (18125-46-7)

Guidance literature:

With pyridoxal 5'-phosphate monohydrate; In aq. buffer; at 40 ℃; for 8h; pH=8.0; Enzymatic reaction;

DOI:10.1002/adsc.201100923

Reference yield: 92.0%

(R)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(4-fluoro-phenyl)-propan-1-one (654054-42-9) → (R)-4-fluorophenylalanine (18125-46-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2003-41470

Reference yield: 81.0%

4-Fluorophenylalanine (51-65-0) → (R)-4-fluorophenylalanine (18125-46-7)

Guidance literature:

With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride; In aq. buffer; at 20 ℃; for 24h; pH=9; enantioselective reaction; Microbiological reaction;

DOI:10.1002/adsc.201600682

upstream raw materials:

(R)-N-acetyl-p-fluorophenylalanine

Sodium; 3-(4-fluoro-phenyl)-2-oxo-propionate

3-(4-Fluoro-phenyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid ethyl ester

(R)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-fluoro-phenyl)-propan-1-one

Downstream raw materials:

(R)-2-Amino-3-(4-fluorophenyl)-1-propanol

N-(N-benzoyl-L-tryptophanyl)-para-fluoro-D-phenylalanine methyl ester

(R)-methyl 2-amino-3-(4-fluorophenyl)propanoate

sodium 3-(4-fluorophenyl)-2-oxopropionate

Refernces

• 1、 Varga, Andrea,Csuka, Pál,Sonesouphap, Orlavanah,Bánóczi, Gergely,To?a, Monica Ioana,Katona, Gabriel,Molnár, Zsófia,Bencze, László Csaba,Poppe, László,Paizs, Csaba. "A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids". . p. 185 - 194. Retrieved 2020/04/28.
• 2、 Walton, Curtis J. W.,Parmeggiani, Fabio,Barber, Janet E. B.,McCann, Jenna L.,Turner, Nicholas J.,Chica, Roberto A.. "Engineered Aminotransferase for the Production of d-Phenylalanine Derivatives Using Biocatalytic Cascades". . p. 470 - 474. Retrieved 2017/12/15.