D-Phenylalanine

Description

D-Phenylalanine, also known as D-alpha-Amino-beta-phenylpropionic acid, is a kind of non-proteinogenic amino acid. The biological function of D-phenylalanine remains unclear. However, it has certain anti-depressant, analgesic activities and pharmacological activity at niacin receptor II. The mechanism action of its analgesic activity seems to originate from its inhibition of enkephalin degradation by the carboxypeptidase A. Enkephalins are part of your body’s natural pain relief system. When they are broken down by enkephalinase, this contributes to the sensation of pain. D-Phenylalanine is specifically thought to be beneficial for reducing feelings of chronic pain. D-phenylalanine has been used with mixed results to treat chronic pain, including pain caused by rheumatoid arthritis. The primary use of D-phenylalanine as a health supplement is the relief of discomfort.

Chemical properties

White crystalline powder

The Uses of D-Phenylalanine

D-Phenylalanine, the stereoisomer of L-Phenylalanine (P319415) has been used in the synthesis of Schaeffer’s acid analogues as important structures in tuberculostatic design. They exhibit the ability to inhibit Mycobacterium tuberculosis type II dehydroquinase.

Definition

ChEBI: D-phenylalanine is the D-enantiomer of phenylalanine. It is a phenylalanine and a D-alpha-amino acid. It is a conjugate base of a D-phenylalaninium. It is a conjugate acid of a D-phenylalaninate. It is an enantiomer of a L-phenylalanine. It is a tautomer of a D-phenylalanine zwitterion.

General Description

D-phenylalanine appears as needles or prisms.

Air & Water Reactions

Water soluble. Aqueous solutions are weakly acidic.

Reactivity Profile

D-alpha-Amino-beta-phenylpropionic acid may be light sensitive. D-alpha-Amino-beta-phenylpropionic acid reacts with strong oxidizing agents, acids and bases. . Act as weak acids in solution.

Fire Hazard

Flash point data for D-alpha-Amino-beta-phenylpropionic acid are not available, however D-alpha-Amino-beta-phenylpropionic acid is probably combustible.

Pharmacokinetics

D-Phenylalanine is the synthetic dextro isomer of phenylalanine, an essential amino acid with anti-depressant and analgesic activities. D-Phenylalanine is converted into tyrosine and tyrosine in turn is converted into L-dopa, norepinephrine, and epinephrine, three key neurotransmitters. As a result this agent is associated with elevated levels of the neurotransmitters dopamine and norepinephrine in the brain, which may alleviate symptoms of depression. In addition, as an inhibitor of enkephalinase, which metabolizes endorphins, D-phenylalanine may be used to treat chronic pain through blocking the break down of endorphins (natural pain killers).

Safety Profile

Mildly toxic by intraperitoneal route. Human systemic effects by ingestion: nausea, hypermotility, diarrhea. When heated to decomposition it emits toxic fumes of NOx.

References

https://www.alfa.com/en/catalog/A10572/
https://en.wikipedia.org/wiki/Phenylalanine
Christianson, D. W., et al. "Binding of D-phenylalanine and D-tyrosine to carboxypeptidase A. " Journal of Biological Chemistry264.22(1989):12849-53.