File:L-Phenylalanin_-_L-Phenylalanine.svg · Wikimedia Commons · See Wikimedia Commons

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phenylalanine

Also known as L-Phe, (S)-2-Amino-3-phenylpropionic acid, (S)-alpha-Amino-beta-phenylpropionic acid, 3-phenyl-L-alanine, beta-Phenyl-L-alanine, F, Phe, β-phenyl-L-alanine

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Chemical data

Formula: C9H11NO2
Molecular weight: 165.19 g/mol
IUPAC name: (2S)-2-azaniumyl-3-phenylpropanoate
SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)[O-])[NH3+]
InChIKey: COLNVLDHVKWLRT-QMMMGPOBSA-N
XLogP: -0.9
Polar surface area: 67.8 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

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Research

106,068 papers

via PubMed

Wikidata facts

Mass: 165.079

Show 9 more facts

Commons category: L-Phenylalanine
chemical formula: C₉H₁₁NO₂
pKa: 9.24
World Health Organisation international non-proprietary name: phenylalanine
canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N
melting point: 283
density: 1.29
isomeric SMILES: N[C@@H](CC1=CC=CC=C1)C(O)=O
NCI Thesaurus ID: C29601

Sources (4)

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Article

13 sections

Contents

History
Dietary sources
Dietary recommendations
Other biological roles
In plants
Biosynthesis
Phenylketonuria
D-, L- and DL-phenylalanine
Commercial synthesis
Derivatives
See also
References
External links

thumb|Phenylalanine ball and stick model spinning Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the biological pigment melanin. It is encoded by the messenger RNA codons UUU and UUC.

Phenylalanine is found naturally in the milk of mammals. It is used in the manufacture of food and drink products and sold as a nutritional supplement as it is a direct precursor to the neuromodulator phenethylamine. As an essential amino acid, phenylalanine is not synthesized de novo in humans and other animals, who must ingest phenylalanine or phenylalanine-containing proteins.