Proline

Proline was the second amino acid synthesized before its presence as a product of the hydrolysis of the protein molecule was established. Willstatter, investigating the position of the carboxyl group in N-methylproline, first obtained this amino acid in 1900. Next year, Fischer published a synthesis of Proline from phthalimide propylmalonic ester by hydrolyzing casein with hydrochloric acid, with consequent esterification of the amino acids and the next distillation of the esters.

Chemical Structure
Structure of Proline

IUPAC Name: (2S)-Pyrrolidine-2-carboxylic acid
Symbol: Three-letter code - Pro. One-letter code - P
Molecular Weight (Molar Mass): 115.13046 g/mol
Molecular Formula (Structural Formula): C5H9NO2
Canonical SMILES: C1CC(NC1)C(=O)O
Isomeric SMILES: C1C[C@H](NC1)C(=O)O
InChIKey Identifier: ONIBWKKTOPOVIA-XWEZEGGSDT
CAS Number: 147-85-3
MDL Number: MFCD00064318
Melting point: 228 °C
Solubility in water: 1623 g/L (25 °C); pKa - 1,99; pKb - 10,60
IR and H1 NMR spectrum: n/a
MSDS (Material Safety Data Sheet): n/a
2D Molfile: Get the molfile
3D PDB file: Get the PDB file
Other names: 2-Pyrrolidinecarboxylic acid; (S)-Pyrrolidine-2-carboxylic acid


In fact, Proline is an essential component of collagen, and therefore is vital for proper functioning of joints and tendons. Besides, this amino acid helps maintain and strengthen heart muscles. Since Proline is a non-essential amino acid, which can be obtained from Glutamic acid, it is not necessary to be obtained additionally from dietary sources. In other words, human body is able to produce enough Proline for its own use. Like many other amino acids, Proline can be easily utilized as an energy source for the body.

Proline is produced when amino acids are transformed each to other and is obtained from the amino acids Glutamine and Ornithine. As for the benefits of this amino acid, Proline is recognized to be beneficial in two critical ways. Firstly, it is responsible for the creation of collagen, and secondly, it helps diminish arterioscleroses.

As you understand, a lack of Proline can cause a number of problems in the human body. For example, this can lead to multiple strains or tears in the soft tissues of the human body. In addition, a lack of this amino acid can also be liable for slower than normal healing.

As for atherosclerosis, Proline prevents its appearance the following way: every time your heart beats, your arteries expand and contract unless some fat is built up onto the walls of the arteries, which condition is known as atherosclerosis. In this case, Proline is able to help your artery be able to effectively stretch out and go back to its normal size and shape. This ability of the amino acid is essential for maintaining the appropriate pressure levels throughout the body, as well as for the long-distance transportation of blood around the circulatory system.