Alanine
Alanine is known to be one of the primary amino acids discovered and synthesized long before its isolation from natural sources. Back in 1850, this amino acid was synthesized by Adolph Strecker from acetaldehyde through its condensation using ammonia and hydrogen cyanide. Only in a quarter of a century, Alanine was discovered in natural sources - in proteins.
Chemical structure of Alanine
Chemical and physical properties of Alanine
IUPAC Name: (2S)-2-Aminopropanoic acid
Symbol: Three-letter code - Ala. One-letter code - A
Molecular Weight (Molar Mass): 89.09318 g/mol
Molecular Formula (Structural Formula): C3H7NO2
Canonical SMILES: CC(C(=O)O)N
Isomeric SMILES: C[C@@H](C(=O)O)N
InChIKey Identifier: QNAYBMKLOCPYGJ-SNQCPAJUDI
CAS Number: 56-41-7
MDL Number: MFCD00064410
Melting point: 314-316 °C
Solubility in water: 166.5 g/1 L (25 °C); pKa - 2,34; pKb - 9,69
2D Molfile: Get the molfile
3D PDB file: Get the PDB file
Other names: L-alpha-Alanine; (S)-Alanine; L-2-Aminopropionic acid; (S)-2-Aminopropionic acid; L-α-Aminopropionic acid
Functions of L-alanine in the body
Alanine is basically a non-essential amino acid sometimes found in high levels in its free state in human plasma. This amino acid is synthesized by reductive amination of pyruvate, and participates in sugar and acid metabolism. It is also known for increasing immunity and providing energy for brain and central nervous system, let alone the muscle tissue. In addition, Alanine plays a central role in glucose-Alanine cycle taking place between tissues and liver.
In a nutshell, Alanine helps your body convert the simple sugar called glucose into energy you need, while eliminating excess toxins from your liver. As you know, amino acids are the building blocks of proteins, thus becoming a key to building muscles, and Alanine is also there in the list, helping protect cells from being damaged during intense physical activity. Then, due to the fact that fluid in the prostate gland contains this amino acid, the suggestions were made that Alanine may help treat benign prostatic hyperplasia, which is the condition in which the prostate enlarges.
In trials designed to assess the effect on high cholesterol levels of combinations of different amino acids, alanine was found to have a cholesterol-reducing effect in the serum of experimental animals (rats), when in combination with arginine and glycine. Levels were reduced by 20% when arginine and alanine alone were administered, and by usually included in amino acid compound tablets; where daily intake levels of between 200 mg and 600 mg daily were suggested.
Dietary sources of L-alanine
As it was mentioned above, Alanine is a non-essential amino acid, i.e. a healthy body can produce it for its own needs. However, it may become an essential amino acid (which means you would need a dietary supplementation) if your body is unable to manufacture it for some reasons. In order to avoid this deficiency, individuals with low-protein diets or eating disorders, as well as those who suffer from liver disease or diabetes, may need to take supplements of this amino acid. To be healthy, human body requires Alanine to process the B vitamin.
Naturally, you are able to get this amino acid from such sources as meat, eggs, poultry, dairy products, and fish. Vegetarians are recommended to eat protein-rich plant foods - for example, avocado, as they also supply Alanine.
beta-Alanine
This is the only naturally occurring β-amino acid. It is found in its free state in the brain. It is a component of carnosine, anserine and of pantothenic acid (vitamin B5) which is itself a component of coenzyme A. The function of carnosine and anserine is unknown.
beta-Alanine is metabolized to acetic acid, and in plants and micro-organisms it is formed from aspartic acis. Therapeutically it is useful to assist in synthesis of pantothenic acid.