Β-Alanine
β-Alanine is a naturally occurring beta amino acid, which is an amino acid in which the amino group is attached to the β-carbon atom instead of the more usual α-carbon atom for alanine. The IUPAC name for β-alanine is 3-aminopropanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter.
Biosynthesis and industrial route
In terms of its biosynthesis, it is formed by the degradation of dihydrouracil and carnosine. β-Alanine ethyl ester is the ethyl ester which hydrolyses within the body to form β-alanine. It is produced industrially by the reaction of ammonia with β-propiolactone.Sources for β-alanine includes pyrimidine catabolism of cytosine and uracil.
Biochemical function
β-Alanine residues are rare. It is a component of the peptides carnosine and anserine and also of pantothenic acid, which itself is a component of coenzyme A. β-alanine is metabolized into acetic acid.Precursor of carnosine
β-Alanine is the rate-limiting precursor of carnosine, which is to say carnosine levels are limited by the amount of available β-alanine, not histidine. Supplementation with β-alanine has been shown to increase the concentration of carnosine in muscles, decrease fatigue in athletes, and increase total muscular work done. Simply supplementing with carnosine is not as effective as supplementing with β-alanine alone since carnosine, when taken orally, is broken down during digestion to its components, histidine and β-alanine. Hence, by weight, only about 40% of the dose is available as β-alanine.Image:Alanines V.1.svg|thumb|left|200px|Comparison of β-alanine with the more customary, chiral, α-amino acid, L-α-alanine
Because β-alanine dipeptides are not incorporated into proteins, they can be stored at relatively high concentrations. Occurring at 17–25 mmol/kg, carnosine is an important intramuscular buffer, constituting 10-20% of the total buffering capacity in type I and II muscle fibres. In carnosine, the pKa of the imidazolium group is 6.83, which is ideal for buffering.
Receptors
Even though much weaker than glycine, β-alanine is an agonist next in activity to the cognate ligand glycine itself, for strychnine-sensitive inhibitory glycine receptors .β-alanine has five known receptor sites, including GABA-A, GABA-C a co-agonist site on NMDA receptors, the aforementioned GlyR site, and blockade of GAT protein-mediated glial GABA uptake, making it a putative "small molecule neurotransmitter."
Athletic performance enhancement
There is evidence that β-alanine supplementation can increase exercise and cognitive performance, for some sporting modalities, and exercises within a 0.5–10 min time frame. β-alanine is converted within muscle cells into carnosine, which acts as a buffer for the lactic acid produced during high-intensity exercises, and helps delay the onset of neuromuscular fatigue.Ingestion of β-alanine can cause paraesthesia, reported as a tingling sensation, in a dose-dependent fashion. Aside from this, no important adverse effect of β-alanine has been reported, however, there is also no information on the effects of its long-term usage or its safety in combination with other supplements, and caution on its use has been advised. Furthermore, many studies have failed to test for the purity of the supplements used and check for the presence of banned substances.
Metabolism
β-Alanine can undergo a transamination reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis.Alternatively, β-alanine can be diverted into pantothenic acid and coenzyme A biosynthesis.