34702-59-5

Basic information

• Product Name: L-PENTAFLUOROPHE
• Synonyms: L-PENTAFLUOROPHENYLALANINE;L-PENTAFLUOROPHE;H-PHE(F5)-OH;H-PENTAFLUORO-PHE-OH;(S)-2-AMINO-3-PENTAFLUOROPHENYL-PROPIONIC ACID;RARECHEM BK PT 0103;PENTAFLUORO-L-PHENYLALANINE;2,3,4,5,6-Pentafluoro-L-phenylalanine
• CAS NO: 34702-59-5
• Molecular Formula: C9H6F5NO2
• Molecular Weight: 255.14
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;a-amino
• Mol File: 34702-59-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 254-257℃
• Boiling Point: 286℃
• Flash Point: 127℃
• Appearance: /
• Density: 1.609
• Vapor Pressure: 0.00124mmHg at 25°C
• Refractive Index: 1.485
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.12±0.40(Predicted)
• Water Solubility: Practically insoluble in water
• CAS DataBase Reference: L-PENTAFLUOROPHE(CAS DataBase Reference)
• NIST Chemistry Reference: L-PENTAFLUOROPHE(34702-59-5)
• EPA Substance Registry System: L-PENTAFLUOROPHE(34702-59-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 34702-59-5(Hazardous Substances Data)

Usage

Description

L-PENTAFLUOROPHE, also known as (S)-2-Amino-3-(perfluorophenyl)propanoic acid, is a unique compound characterized by the presence of a perfluorophenyl group attached to an amino acid backbone. This fluorine-containing molecule exhibits distinct chemical and biological properties, making it a valuable subject for research and development in various fields.

Uses

Used in Pharmaceutical and Biomedical Research:
L-PENTAFLUOROPHE is used as a key component in the synthesis of fluorine-containing dipeptides for their potential applications in the diagnosis and treatment of cancer and other related conditions. The incorporation of fluorine atoms into these dipeptides can enhance their stability, bioavailability, and interaction with biological targets, leading to improved diagnostic and therapeutic outcomes.
Used in Cancer Diagnostics:
L-PENTAFLUOROPHE is utilized in the development of novel diagnostic agents that can specifically target and image cancer cells. The unique properties of the perfluorophenyl group allow for the design of molecules with high affinity for cancer biomarkers, enabling the detection and monitoring of cancer progression with high sensitivity and specificity.
Used in Drug Design and Development:
The distinctive features of L-PENTAFLUOROPHE make it a promising candidate for the design of new drugs targeting various diseases, including cancer. Its fluorine-containing structure can be exploited to modulate the pharmacokinetics, pharmacodynamics, and target selectivity of drug molecules, potentially leading to the discovery of more effective and safer therapeutic agents.

InChI:InChI=1/C9H6F5NO2/c10-4-2(1-3(15)9(16)17)5(11)7(13)8(14)6(4)12/h3H,1,15H2,(H,16,17)/t3-/m1/s1

Upstream product

• 3321-96-8 (R,S)-pentafluoropenylalanine 
• 49759-67-3 2S-2-benzyloxycarbonylamino-2-(pentafluorophenyl-methyl)-acetic acid 
• 151962-26-4 (R,S)-N-phenylacetyl-pentafluorophenylalanine 
• 1765-40-8 (bromomethyl)pentafluorobenzene 
• 119838-19-6 (2R,5R)-2-t-butyl-1-t-butyloxycarbonyl-3-methyl-5-pentafluorobenzyl-4-imidazolidinone 
• 771-56-2 2,3,4,5,6-pentafluorotoluene 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 18944-76-8 2-acetylamino-2-pentafluorophenylmethyl-malonic acid diethyl ester 
• 136207-26-6 (S)-2-((tert-butoxycarbonyl)amino)-3-(perfluorophenyl)propanoic acid 
• 49759-53-7 2-Benzyloxycarbonylamino-2-pentafluorophenylmethyl-malonic acid dimethyl ester 
• 50582-25-7 2-Benzyloxycarbonylamino-2-pentafluorophenylmethyl-malonic acid monomethyl ester 
• 49759-57-1 2-Benzyloxycarbonylamino-3-pentafluorophenyl-propionic acid methyl ester 
• 34234-46-3 2,3,4,5,6-pentafluoro-trans-cinnamic acid 

Downstream Products

• 1601485-95-3 C₁₇H₁₉F₅N₂O₂S₂ 
• 1207604-38-3 (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(perfluorophenyl)propanamido)-3-(perfluorophenyl)propanoate 
• 198701-52-9 (S)-2-Amino-3-pentafluorophenyl-propionic acid methyl ester 

Relevant articles and documents

Method for Preparing Unnatural Amino Acids

The present invention relates to a manufacturing method of unnatural amino acids and unnatural amino acids manufactured thereby. Specifically, the present invention relates to an asymmetric synthesis method which can manufacture unnatural amino acids having significantly high optical purity, and to the unnatural amino acids manufactured thereby. A manufacturing method of unnatural amino acids represented by chemical formula 6 or chemical formula 7 comprises the steps of: synthesizing a compound represented by chemical formula 4 or chemical formula 5; manufacturing a diol compound; and manufacturing a carboxylic acid compound.COPYRIGHT KIPO 2016

Phenylalanine ammonia-lyase: The use of its broad substrate specificity for mechanistic investigations and biocatalysis - Synthesis of L-arylalanines

Several fluoro-and chlorophenylalanines were found to be good substrates of phenylalanine ammonialyase (PAL/EC 4.3.1.5) from parsley. The enantiomerically pure L-amino acids were obtained in good yields by reaction of the corresponding cinnamic acids with 5M ammonia solution (buffered to pH 10) in the presence of PAL. The kinetic constants for nine different fluoro-and chlorophenylalanines do not provide a rigorous proof for but are consistent with the previously proposed mechanism comprising an electrophilic attack of the methylidene-imidazolone cofactor of PAL at the aromatic nucleus as a first chemical step. In the resulting Friedel-Crafts-type σ complex the β-protons are activated for abstraction and consequently the pro-S is abstracted by an enzymic base. Results from semi-empirical calculations combined with a proposed partial active site model showed a correlation between the experimental kinetic constants and the change in polarization of the pro-S Cβ-H bond and heat of formation of the σ complexes, thus making the electrophilic attack at the neutral aromatic ring plausible. Furthermore, while 5-pyrimidinylalanine was found to be a moderately good substrate of PAL, 2-pyrimidinylalanine was an inhibitor.

HOMOCHIRAL HETEROORGANIC ANALOGS OF NATURAL COMPOUNDS. III. BIOCATALYTIC METHOD OF OBTAINING HOMOCHIRAL FLUORINE-CONTAINING (R)- AND (S)-PHENYLALANINES AND (S,R)- AND (R,S)-PHENYLSERINES

A convenient biocatalytic method of obtaining homochiral (S)- and (R)-threo-β-(4-fluorophenyl)serine and -2-, -3-, and 4-fluoro- and -2,3,4,5,6-pentafluorophenylalanines by the enantioselective hydrolysis of their racemic N-phenylacetyl derivatives under the action of Escherichia coli penicillin acylase is proposed.