L-alanine
Alanine (IUPAC-IUBMB abbreviation: Ala and A) represents an α-amino acid, with its L enantiomer serving as one of the twenty-two proteinogenic amino acids encoded within messenger RNA by the codons GCU, GCC, GCA, and GCG. Notably, characterized by an aliphatic nonpolar side chain, it ranks among the most prevalent amino acids found in proteins, alongside serine, leucine, and glycine, contributing significantly to the structural and functional diversity of proteins in various biological processes.
In the natural milieu, the D-alanine enantiomer assumes a critical role, particularly in the construction of peptidoglycan, the primary component of bacterial cell walls. The formation of D-alanine from L-alanine is facilitated by the action of an isomerase, alanine racemase, emphasizing its significance in fundamental biological processes, notably in bacterial cell wall biosynthesis and integrity maintenance.
Within the context of cellular metabolism, L-alanine is synthesized in muscle cells from pyruvate in the presence of glutamate, a process known as transamination. In the liver, alanine undergoes transformation into pyruvate. Furthermore, the enzyme alanine aminotransferase (ALAT) catalyzes the reaction involving the transfer of the amino group from alanine to α-ketoglutarate, contributing to the intricate network of biochemical pathways governing amino acid metabolism. As an aliphatic amino acid, alanine plays an integral role in various biochemical processes, underscoring its significance in cellular function and metabolic homeostasis.
Alanine is a non-essential amino acid, meaning that the body can synthesize it and it is not necessarily obtained through dietary sources. It is found in a variety of foods, with particularly high concentrations in meats.
The body utilizes alanine for energy production, tissue repair, and the synthesis of other proteins. Furthermore, it plays a crucial role in the functioning of the immune system and the central nervous system.
Here are some of the functions of alanine in the body:
- Energy production: Alanine serves as an energy source for both muscles and the brain.
- Tissue repair: It aids in the repair of damaged muscle and hepatic tissues.
- Protein synthesis: Alanine is one of the 20 amino acids that constitute proteins.
- Immune system function: It is involved in the production of white blood cells, which help combat infections.
- Central nervous system function: Alanine contributes to the production of neurotransmitters, which are chemicals enabling communication between nerve cells.
Alanine is generally well-tolerated by most individuals. However, high doses of alanine may lead to side effects such as stomach discomfort, nausea, and vomiting.
Here are some examples of foods rich in alanine:
- Meats: beef, chicken, pork, lamb
- Fish: tuna, salmon, mackerel
- Eggs
- Dairy products: cheese, yogurt, milk
- Vegetables: soy, lentils, beans
- Nuts: almonds, cashews, pistachios
Alanine is an essential amino acid crucial for overall body health. It contributes to various vital functions, including energy production, tissue repair, protein synthesis, and the proper functioning of the immune system and the central nervous system.
Synonyms :
- L-ALANINE
- Ala
- A
Config Rule :
config('L-alanine',[
substituent(aminoacid_L_backbone),
substituent(methyl),
linkage(from(aminoacid_L_backbone,car(1)),
to(methyl,car(1)),
down,single)]).
%%%% Substituent Config Rules for compound 'L-alanine' %%%%
config(aminoacid_L_backbone,[
left(amino),
right(hyd),
top(carboxyl),
center(car(1))]).
Smiles String :
[C@2H]([NH3+])([C](=[O])[O-])[CH3] 'L-alanine'
Fischer Diagram :
Terminal :
% 'L-alanine'
c(1,12,(0,chiral))-[n(1,left)~,h(1,right)~,c(2,up)~,c(3,down)~],
c(2,12,(0,nonchiral))-[o(1,nil)?,o(2,nil)?,c(1,down)~],
c(3,12,(0,nonchiral))-[h(5,left)~,h(6,right)~,c(1,up)~,h(7,down)~],
h(1,1,(0,nonchiral))-[c(1,left)~],
h(2,1,(0,nonchiral))-[n(1,right)~],
h(3,1,(0,nonchiral))-[n(1,down)~],
h(4,1,(0,nonchiral))-[n(1,up)~],
h(5,1,(0,nonchiral))-[c(3,right)~],
h(6,1,(0,nonchiral))-[c(3,left)~],
h(7,1,(0,nonchiral))-[c(3,up)~],
n(1,14,(1,nonchiral))-[h(2,left)~,c(1,right)~,h(3,up)~,h(4,down)~],
o(1,16,(-5.0E-01,nonchiral))-[c(2,nil)?],
o(2,16,(-5.0E-01,nonchiral))-[c(2,nil)?]