Description
As an essential amino acid, phenylalanine is necessary for the production of tyrosine in human body, which cannot be synthesized from more basic substances in humans and other animals, meaning that it is obtained only by ingestion of phenylalanine or phenylalanine- containing proteins, which is particularly rich in eggs, chicken, liver, beef, breast milk of mammals, and soybeans, etc. There are three forms of phenylalanine: L-phenylalanine, the natural form found in protein-rich foods, D-phenylalanine, the synthetic mirror image and DL-Phenylalanine (DLPA), the mixture of both forms made in the laboratory that can maximize benefits. DLPA is manufactured for medical, feed, and nutritional applications, which can be used to produce food and drink products. It is marketed as a nutritional supplement due to its reputed analgesic and antidepressant effects. Besides, it can be applied for depression, attention deficit-hyperactivity disorder (ADHD), Parkinson's disease, chronic pain, osteoarthritis, rheumatoid arthritis, alcohol withdrawal symptoms, and a skin disease called vitiligo.
References
https://en.wikipedia.org/wiki/Phenylalanine
http://www.livestrong.com/article/501701-what-are-the-benefits-of- dl-phenylalanine/
http://www.webmd.com/vitamins-supplements/ingredientmono-653- phenylalanine.aspx? activeingredientid=653&activeingredientname=phenylalanine
Chemical Properties
White crystalline powder
Chemical Properties
DL-Phenylalanine has a sweet taste. It is an essential amino acid that plays a key role in the biosynthesis of other amino
acids and some neurotransmitters.
Occurrence
Phenylalanine is the most commonly found aromatic amino acid in proteins and enzymes with a molar ratio of
3.5% compared to the other amino acids, about double the amount of any other aromatic amino acid. Reported found in white bread,
macaroni, egg noodles, corn flakes, corn grits, oatmeal, wheat bran, wheat flakes, shredded wheat, barley, brown rice, rye flour,
whole grain wheat flour, buttermilk, blue cheese, cheddar cheese, cottage cheese, cream cheese, parmesan cheese, bacon, cured ham,
frankfurters, pork sausage, canned red kidney beans, canned sweet corn, canned peas, canned lima beans, canned potatoes, canned
asparagus, canned snap beans, canned beets, beef, lamb, fresh ham, veal round, beef liver, chicken, chicken liver, turkey and other
natural sources.
Uses
DL-Phenylalanine may be used in the synthesis of ternary piroxicam (Pir; 4-hydroxy-2-methyl-
N-(2-pyridyl)-2
H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) complexes of Fe(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II).
Uses
Component of the artificial sweetner aspartame, q.v.; nutrient.
Uses
DL-Phenylalanine is used torelieve cases of minor depressionand other mood issues as well as and physical discomforts and pain. It is also used in acupunctureanesthesia, alcohol withdrawal.
Definition
ChEBI: An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.
Preparation
By microbial bioengineered process.
General Description
Phenylalanine is an amino acid. It participates in the preparation of ternary piroxicam complexes of Fe(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II). Characterization of these complexes by elemental analyses, molar conductance, IR, UV-Vis, magnetic moment, diffuse reflectance and X-ray powder diffraction methods has been conducted. Crystalline DL-phenylalanine was prepared by its reduction in silica gel by solubility method.
reaction suitability
reaction type: solution phase peptide synthesis
Side effects
When taken by mouth: L-phenylalanine is commonly consumed in foods. L-phenylalanine, D-phenylalanine, and DL-phenylalanine are possibly safe when used as medicine, short-term. Side effects might include anxiety, headache, and constipation. When applied to the skin: Phenylalanine cream is possibly safe when used in the short-term.
Purification Methods
dl-Phenylalanine crystallises from H2O or H2O/EtOH in large plates and is dried under vacuum over P2O5. S-Phenylalanine ethyl ester hydrochloride has m 156-158o and [ ] D -7.8o (c 2, H2O) after crystallisation from EtOH/Et2O [Billimoria & Cook J Chem Soc 2328 1949, Beilstein 14 IV 1556]. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2156-2175 1961, Beilstein 14 III 1229, 14 IV 1553.]
