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Phenylalanine ball and stick model spinning. Phenylalanine (symbol Phe or F) [3] is an essential α-amino acid with the formula C 9 H 11 NO 2.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.
Pyrrolysine (considered the 22nd amino acid), [3] which is proteinogenic only in certain microorganisms, is not used by and therefore non-essential for most organisms, including humans. The limiting amino acid is the essential amino acid which is furthest from meeting nutritional requirements. [ 4 ]
Phenylalanine is a large, neutral amino acid (LNAA). LNAAs compete for transport across the blood–brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). If phenylalanine is in excess in the blood, it will saturate the transporter. Excessive phenylalanine levels tend to decrease the levels of other LNAAs in the brain.
“The body naturally can make tyrosine from [another amino acid] phenylalanine, and it can be obtained directly through diet from a variety of foods,” says Pumper.
In mammals it is created from -lactate and L-phenylalanine by the cytosol nonspecific dipeptidase (CNDP2) protein. [1] It is classified as N-acyl-alpha-amino acid and pseudodipeptide. [11] It has also been reported that as an additive, N-L-lactoyl phenylalanine improves the taste of food, conferring an umami flavor. [12]
Aspartame is an artificial non-saccharide sweetener commonly used as a sugar substitute in foods and beverages. [4] 200 times sweeter than sucrose, it is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. [4]
This metabolic pathway is nonexistent in the healthy body, but becomes important after peripheral l-DOPA administration in patients with Parkinson's disease or in the rare cases of patients with AADC enzyme deficiency. [11] l-Phenylalanine, l-tyrosine, and l-DOPA are all precursors to the biological pigment melanin.
Tetrahydrobiopterin deficiency (THBD, BH 4 D) is a rare metabolic disorder that increases the blood levels of phenylalanine.Phenylalanine is an amino acid obtained normally through the diet, but can be harmful if excess levels build up, causing intellectual disability and other serious health problems.
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