Phenylalanine

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The alpha-amino acid Phenylalanine exists in two forms, the D- and L- forms, which are enantiomers (mirror-image molecules) of each other. It has a benzyl side chain. Its name comes from its chemical structure consisting of a phenyl group substituted for one of the hydrogens in the side chain of alanine. Because of its phenyl group, phenylalanine is an aromatic compound. At room temperature, it is a white, powdery solid. L-Phenylalanine (LPA) is an electrically neutral amino acid, one of the twenty common amino acids used to biochemically form proteins, coded for by DNA. Its enantiomer, D-phenylalanine (DPA), can be synthesized artificially.

Related Topics:
Amino acid - Enantiomer - Molecule - Benzyl - Chemical structure - Phenyl group - Alanine - Aromatic compound - Room temperature - Solid - Protein - DNA

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L-phenylalanine is used in living organisms, including the human body, where it is an essential amino acid. L-phenylalanine can also be converted into L-tyrosine, another one of the twenty protein-forming amino acids. L-tyrosine is converted into L-DOPA, norepinephrine, and epinephrine. D-phenylalanine can be converted only into phenylethylamine.

Related Topics:
Organism - Essential amino acid - Tyrosine - L-DOPA - Norepinephrine - Epinephrine - Phenylethylamine

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The genetic disorder phenylketonuria is an inability to metabolize phenylalanine.

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The synthesized mix DL-Phenylalanine (DLPA), which is a combination of the D- and L- forms, is used as a nutritional supplement.

Related Topics:
DL-Phenylalanine - Nutritional supplement

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Phenylalanine is part of the composition of aspartame, a common sweetener found in prepared foods (particularly soft drinks, and gum). Due to phenylketonuria, products containing aspartame usually have a warning label stating that they contain phenylalanine, in compliance with U.S. FDA guidelines.

Related Topics:
Aspartame - Sweetener - Phenylketonuria - FDA

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The genetic codon for phenylalanine was the first to be discovered. Marshall W. Nirenberg discovered that, when he inserted m-RNA made up of multiple uracil repeats into E. coli, the bacterium produced a new protein, made up solely of repeated phenylalanine amino acids.

Related Topics:
Codon - Marshall W. Nirenberg - RNA - Uracil

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Phenylalanine uses the same active transport channel as tryptophan to cross the blood-brain barrier, and in large quantities interferes with the production of serotonin.

Related Topics:
Tryptophan - Blood-brain barrier - Serotonin

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