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Amino acid

life science Maturity 11-13 Next article →

Amino acids are organic compounds that serve as the fundamental building blocks of life. They are defined by containing both an amino functional group and a carboxylic acid functional group. While nature contains over 500 different amino acids, only 22 are considered proteinogenic. These 22 specific amino acids are incorporated into proteins via the genetic code of life.

L-amino acid structure
L-amino acid structure

In the human body, amino acid residues form the second-largest component of muscles and tissues, surpassed only by water. Beyond building structures, they participate in essential processes like biosynthesis and neurotransmitter transport. Scientists believe they played a vital role in the very emergence of life on Earth.

To understand how proteins form, one must look at the molecular mechanism of connection. Proteins are built from many amino acids joined in a linear structure called a peptide.

Peptidformationball
Peptidformationball

This happens through a process where the amino group of one amino acid forms a bond with the carboxyl group of another. This specific arrangement was proposed independently by Emil Fischer and Franz Hofmeister in 1902. Most proteinogenic amino acids are alpha (α)-amino acids, meaning the functional groups are attached to the same central carbon atom. This central atom is known as the α-carbon. In most cases, this carbon is stereogenic, meaning it has a specific spatial orientation. Except for glycine, all proteinogenic amino acids possess an L-configuration, often called "left-handed" enantiomers.

Amino acids are classified by their chemical properties, particularly the nature of their side chains, also called R groups.

ProteinogenicAminoAcids
ProteinogenicAminoAcids

These side chains determine how an amino acid behaves in a biological system. Some side chains are polar and uncharged, such as serine, threonine, asparagine, and glutamine. These molecules readily form hydrogen bonds with water. Other amino acids are hydrophobic, or nonpolar. These side chains do not ionize easily and drive the folding of proteins. In a water-based environment, hydrophobic residues like leucine, isoleucine, and valine tend to bury themselves in the protein's interior. This movement is a primary force that allows proteins to fold into functional three-dimensional shapes.

Another major category involves charged side chains, which are essential for solubility and protein stability.

Histidine lysine arginine sidechains
Histidine lysine arginine sidechains

At a neutral pH of 7.4, five amino acids possess a charge. The two negatively charged amino acids, known as anions, are aspartate and glutamate. On the opposite side, three amino acids act as cations, or positively charged molecules: arginine, lysine, and histidine. These charges allow for the formation of salt bridges, which are electrostatic contacts that maintain protein structures. For example, proteins designed to bind positively charged molecules often have surfaces rich in negatively charged aspartate and glutamate. This chemical logic extends to how proteins interact with membranes and other molecules.

The history of discovering these molecules spans over a century of chemical research.

Amino acids in food and blood
Amino acids in food and blood

The first amino acid, asparagine, was isolated from asparagus in 1806 by French chemists Louis-Nicolas Vauquelin and Pierre Jean Robiquet. This was followed by the discovery of cystine in 1810. By 1820, researchers had identified glycine and leucine. It took much longer to complete the set of common amino acids. In 1935, William Cumming Rose discovered threonine. Rose was also responsible for identifying essential amino acids and establishing the minimum daily requirements needed for optimal growth.

Some amino acids act as unique outliers due to their specific chemical structures.

Amino acid zwitterions
Amino acid zwitterions

Glycine is unique because its side chain is simply a hydrogen atom, providing it with great flexibility in protein folding. Proline is another outlier; its side chain joins back onto the amino group, making the protein chain particularly inflexible. Cysteine is notable for its ability to form covalent disulfide bonds with other cysteine residues. These bonds are essential for the stability of proteins and the formation of antibodies. Additionally, rare amino acids like selenocysteine and pyrrolysine are incorporated into proteins by ribosomes even though they are not directly encoded by DNA.

Finally, the way amino acids carry electrical charges is central to their behavior in water. In aqueous solutions near a neutral pH, amino acids exist in a zwitterionic form.

A zwitterion is a molecule that carries both a positive and a negative charge simultaneously. This occurs because the amino group becomes protonated while the carboxyl group becomes deprotonated. This balanced state is energetically favored in the body. Understanding these acid-base behaviors and the various ways side chains can be modified allows scientists to grasp how complex biological systems function at the most basic level.

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🖼️ Images & Media (11)
File:L-amino acid structure.svg
L-amino acid structure.svg
File:ProteinogenicAminoAcids.svg
ProteinogenicAminoAcids.svg
File:Histidine lysine arginine sidechains.svg
Histidine lysine arginine sidechains.svg
File:Amino acid zwitterions.svg
Amino acid zwitterions.svg
File:Bronsted_character_of_ionizing_groups_in_proteins.png
Bronsted_character_of_ionizing_groups_in_p...
File:Titration Curves of 20 Amino Acids Organized by Side Chain.png
Titration Curves of 20 Amino Acids...
File:Amino acids in food and blood.png
Amino acids in food and blood.png
File:Strecker amino acid synthesis scheme.svg
Strecker amino acid synthesis scheme.svg
File:Peptidformationball.svg
Peptidformationball.svg
File:Amino acid catabolism revised.png
Amino acid catabolism revised.png
File:AAcomplexation.png
AAcomplexation.png
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