L-4-BENZOYLPHENYLALANINE

L-4-BENZOYLPHENYLALANINE Property

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

Safety Statements 

24/25

HS Code 

29225090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

L-4-BENZOYLPHENYLALANINE Chemical Properties,Usage,Production

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