151911-33-0

Basic information

• Product Name: (S)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID
• Synonyms: H-BETA-PHE(4-F)-OH;H-D-PHG(4-F)-(C*CH2)OH;(S)-BETA-(P-FLUOROPHENYL)ALANINE;(S)-B-(P-FLUOROPHENYL)-B-ALANINE;(S)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID;(S)-4-FLUORO-BETA-PHENYLALANINE;RARECHEM LK HC T330;(S)-beta-4-Fluorophenylalanine
• CAS NO: 151911-33-0
• Molecular Formula: C₉H₁₀FNO₂
• Molecular Weight: 183.18
• Product Categories: 3-Amino-3-phenylpropionic Acid Analogs;3-Amino-3-phenylpropanoic Acid Analogs;B-Amino
• Mol File: 151911-33-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 308.829 °C at 760 mmHg
• Flash Point: 140.575 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 0.000287mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.66±0.10(Predicted)
• CAS DataBase Reference: (S)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID(151911-33-0)
• EPA Substance Registry System: (S)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID(151911-33-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 151911-33-0(Hazardous Substances Data)

Usage

General Description

(S)-3-Amino-3-(4-fluoro-phenyl)-propionic acid, also known as L-4-FluoroPhenylalanine, is a chemical compound that contains fluorine and phenyl groups. It is an amino acid derivative, where the amino group is located on the third carbon of the propionic acid chain. Its chemical formula is C9H10FNO2, illustrating that it contains nine carbon atoms, ten hydrogen atoms, one nitrogen atom, two oxygen atoms, and one fluorine atom. Its unique structure and properties have made it of interest in various pharmaceutical research studies, particularly in the synthesis and study of bioactive molecules and proteins.

InChI:InChI=1/C9H10FNO2/c10-7-3-1-6(2-4-7)8(11)5-9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1

Upstream product

• 218166-05-3 3-amino-3-(4-fluorophenyl)propionic acid ethyl ester 
• 325-89-3 3-amino-3-(4-fluorophenyl)propanoic acid 
• 171002-17-8 β-(N-phenylacetylamino)-β-(4-fluorophenyl)propionic acid 
• 1393363-59-1 tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-fluorophenyl)propanoate 
• 1393363-74-0 tert-butyl (S)-3-amino-3-(4'-fluorophenyl)propanoate 
• 350490-14-1 tert-butyl (2E)-3-(4-fluorophenyl)-2-propenoate 
• 103-81-1 Benzeneacetamide 
• 459-57-4 4-fluorobenzaldehyde 
• 459-32-5 4-fluorocinnamic acid 
• 51-65-0 4-Fluorophenylalanine 
• 1999-00-4 ethyl 3-(4'-fluorophenyl)-3-oxopropionate 

Downstream Products

• 852443-89-1 (3S)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-fluorophenol)propanoic acid 

Relevant articles and documents

Glutamate as an Efficient Amine Donor for the Synthesis of Chiral β- and γ-Amino Acids Using Transaminase

A recyclable glutamate amine donor system employing transaminase (TA), glutamate dehydrogenase (GluDH) and mutant formate dehydrogenase (FDHm) was developed, wherein amine donor Glu was regenerated using GluDH and thereby circumvented the inhibition of TA by α-ketoglutarate. Various enantiopure β-, γ-amino acids, and amines were successfully synthesized with high conversions and excellent enantiomeric excess using this system.

The bacterial ammonia lyase EncP: A tunable biocatalyst for the synthesis of unnatural amino acids

Enzymes of the class I lyase-like family catalyze the asymmetric addition of ammonia to arylacrylates, yielding high value amino acids as products. Recent examples include the use of phenylalanine ammonia lyases (PALs), either alone or as a gateway to deracemization cascades (giving (S)- or (R)-α-phenylalanine derivatives, respectively), and also eukaryotic phenylalanine aminomutases (PAMs) for the synthesis of the (R)-β-products. Herein, we present the investigation of another family member, EncP from Streptomyces maritimus, thereby expanding the biocatalytic toolbox and enabling the production of the missing (S)-β-isomer. EncP was found to convert a range of arylacrylates to a mixture of (S)-α- and (S)-β-arylalanines, with regioselectivity correlating to the strength of electron-withdrawing/-donating groups on the ring of each substrate. The low regioselectivity of the wild-type enzyme was addressed via structure-based rational design to generate three variants with altered preference for either α- or β-products. By examining various biocatalyst/substrate combinations, it was demonstrated that the amination pattern of the reaction could be tuned to achieve selectivities between 99:1 and 1:99 for β:α-product ratios as desired.

Asymmetric synthesis of β-fluoroaryl-β-amino acids

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl) amide to a range of β-fluoroaryl-α,β-unsaturated esters gave the corresponding β-amino esters with high diastereoselectivity and in good isolated yields. Sequential treatment of the resulta