L-4-BENZOYLPHENYLALANINE Chemical Properties

Boiling point:

467.6±40.0 °C(Predicted)

Density 

1.249±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMF: insol; DMSO: insol; Ethanol: insol; PBS (pH 7.2): insol

form 

A solid

pka

2.16±0.10(Predicted)

color 

White to light yellow

InChI

InChI=1S/C16H15NO3/c17-14(16(19)20)10-11-6-8-13(9-7-11)15(18)12-4-2-1-3-5-12/h1-9,14H,10,17H2,(H,19,20)/t14-/m0/s1

InChIKey

TVIDEEHSOPHZBR-AWEZNQCLSA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(C(=O)C2=CC=CC=C2)C=C1)N

Safety Information

Safety Statements 

24/25

HS Code 

29225090

L-4-BENZOYLPHENYLALANINE Usage And Synthesis

Chemical Properties

Off-white solid

Uses

4-Benzoyl-L-phenylalanine is a photoreactive amino acid which can easily be incorporated into a peptide by solid-phase synthesis and finds application as phtolabel. It is an important raw material as well as an intermediate in organic synthesis.

Synthesis

The general procedure for the synthesis of (S)-2-amino-3-(4-benzoylphenyl)propionic acid from L-phenylalanine and benzoyl chloride was as follows: in a reaction tube fitted with a screw cap and polytetrafluoroethylene (PTFE)-faced rubber lining, L-phenylalanine (16.5 mg, 0.1 mmol) was added followed by trifluoromethanesulfonic acid (0.5 mL). After the solution was homogenized, benzoyl chloride (8 eq.) was added slowly at 0 °C. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the mixture was poured into a mixture of cold water and ethyl acetate. The organic layer was separated, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (eluent ratio ethyl acetate:methanol:water=8:1:0.5) to give a colorless amorphous product (7.5 mg, 28% yield, 98% enantiomeric excess value). The structure of the product was confirmed by 1H-NMR (CD3OD): δ 7.76 (d, 2H, J=8.6 Hz, Ar), 7.75 (d, 2H, J=8.6 Hz, Ar), 7.64 (t, 1H, J=7.4 Hz, Ar), 7.52 (t, 2H, J=7.4 Hz, Ar), 7.47 (d, 2H, J=8.0 Hz, Ar ), 3.83(m, 1H, Hα), 3.35(m, 1H, Hβ), 3.09(m, 1H, Hβ).

storage

Store at +4°C

References

[1] Molecules, 2013, vol. 18, # 7, p. 8393 - 8401
[2] Heterocycles, 2013, vol. 87, # 10, p. 2119 - 2126

L-4-BENZOYLPHENYLALANINE(104504-45-2)Related Product Information

• 4-Methylphenyl-L-alanine
• L-PHE(4-COCH3)
• H-PHE-ALA-OH
• PHE-GLY-GLY
• H-4-NITRO-PHE-OET HCL
• L-4-Iodophenylalanine
• 4-Methoxy-L-phenylalanine
• L-4-Chlorophenylalanine
• L-4-Fluorophenylalanine
• L-4-TERT-BUTYL-PHE
• H-Phe-D-Phe-OMe.HCl
• L-4-Nitrophenylalanine methyl ester hydrochloride
• 4-AMINOTETRAHYDROPYRAN-4-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
• L-4-Cyanophenylalanine
• 4-Amino-L-phenylalanine hydrochloride
• METHYL 4-BROMO-L-PHENYLALANINATE HYDROCHLORIDE
• H-Phe(4-Cl)-OMe.HCl
• 4-Amino-L-phenylalanine