Showing chemical card for L-(-)-Phenylalanine (CFc000333687)
Record Information
Version
1.0
Creation Date
Update Date
2022-09-14 05:14:01 UTC
Chemfont ID
CFc000333687
Molecule Identification
Common Name
L-(-)-Phenylalanine
Definition
Phenylalanine, abbreviated Phe or F, is a neutral, nonpolar, hydrophobic, essential amino acid. It is the precursor of the amino acid tyrosine, a precursor of the skin pigment melanin and a precursor of catecholamines that include tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma and is found naturally in mammalian breast milk. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in several high protein foods, such as meat, cottage cheese, and wheat germ. An additional dietary source of phenylalanine is artificial sweeteners containing aspartame. Generally, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Phenylalanine also has some potential benefits. Phenylalanine can act as an analgesic, providing relief for premenstrual syndrome and may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS) for Parkinson's patients. Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For some tumours that use more phenylalanine than others (such as melatonin-producing tumours called melanomas) may benefit from low phenylalanine diets.
Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
