Phenylalanine

Phenylalanine was found in the seedlings of Lupinus Zuteus by Schulze and Barbieri in 1879 - before it was discovered among the products of hydrolysis of proteins. Almost a century later, a Japanese company started production of Phenylalanine by fermentation.

Chemical Structure
Structure of Phenylalanine

IUPAC Name: (2S)-2-Amino-3-phenylpropanoic acid
Symbol: Three-letter code - Phe. One-letter code - F
Molecular Weight (Molar Mass): 165.18914 g/mol
Molecular Formula (Structural Formula): C9H11NO2
Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N
Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)N
InChIKey Identifier: COLNVLDHVKWLRT-KMJKUPBBDK
CAS Number: 63-91-2
MDL Number: MFCD00064227
Melting point: 270-275 °C
Solubility in water: 27 g/L (20 °C); pKa - 1,83; pKb - 9,13
IR and H1 NMR spectrum: n/a
MSDS (Material Safety Data Sheet): n/a
2D Molfile: Get the molfile
3D PDB file: Get the PDB file
Other names: L-beta-Phenylalanine; L-2-Amino-3-phenylpropionic acid; (S)-alpha-Amino-benzenepropanoic acid; (S)-alpha-Aminohydrocinnamic acid; (S)-alpha-Amino-beta-phenylpropionic acid; Phenyl-alpha-alanine; (-)-beta-Phenylalanine; beta-Phenyl-alpha-alanine; beta-Phenyl-L-alanine; 3-Phenyl-L-alanine; L-beta-Phenylalanine; (S)-Phenylalanine; 3-Phenylalanine


Actually, Phenylalanine is a precursor of Tyrosine, combined with which it leads to the formation of adrenaline. In turn, adrenaline is converted into a brain chemical utilized to produce noradrenaline responsible for promoting mental alertness and memory, and also for the elevation of mood and for the suppression of appetite.

In fact, Phenylalanine is an essential amino acid, also acting as a building block for proteins, indicating that, although your body requires this amino acid for health, it is unable to produce it by itself. So, you have the only way to satisfy your demand in Phenylalanine - to get it from food.

Since noradrenaline affects mood, various forms of phenylalanine have been suggested to treat such conditions as lack of energy, memory problems, depression, confusion, decreased alertness, and lack of appetite, all of which are considered to be caused by the Phenylalanine deficiency.

However, there is a rare metabolic disorder - phenylketonuria, which occurs in people missing an enzyme that the human body requires to utilize Phenylalanine. As a result, the disorder causes high levels of this amino acid, which in turn can lead to severe, irreversible mental retardation if is not treated before three weeks of age. In our country, all newborns are tested for this disorder during the first 2-3 days of life. People suffering from it have to eat a diet avoiding Phenylalanine.

According to a number of researches, this amino acid can help treat chronic pain, strengthen the effect of UVA radiation for people with vitiligo, and even Parkinson's disease - there was a study on animals suggesting that Phenylalanine is able to improve walking disabilities, rigidity, speech difficulties, and depression caused by Parkinson's disease. Finally, Phenylalanine is considered to be helpful in treating depression, because this amino acid stimulates the production of brain chemicals like dopamine and norepinephrine.