Technical Information Amino Acids Proline

Proline

Proline, symbolized as Pro or P, is categorized as an organic acid and falls under the class of proteinogenic amino acids. However, unlike other amino acids, it lacks the amino group -NH2 and instead possesses a secondary amine group. Under biological conditions, the secondary amine nitrogen exists in the protonated form (NH2+), while the carboxyl group is deprotonated (-COO-). The α carbon's "side chain" is connected to the nitrogen, forming a pyrrolidine loop and classifying proline as an aliphatic amino acid. In humans, proline is considered non-essential, indicating that the body can synthesize it from the non-essential amino acid L-glutamate. Proline and its derivatives find frequent use as asymmetric catalysts in proline organocatalysis reactions. Notable examples include the CBS reduction and proline-catalyzed aldol condensation. L-Proline, in addition to its catalytic properties, serves as an osmoprotectant and finds application in various pharmaceutical and biotechnological fields. Proline supplementation in the growth medium used for plant tissue culture has been observed to enhance growth. This effect may be attributed to proline's ability to aid plants in tolerating the stresses associated with tissue culture. The codons CCU, CCC, CCA, and CCG all encode proline.

Structure
CAS Number 147-85-3
Classification

Hydrophobic amino acids (nonpolar amino acids), including

Phenylalanine

Alanine

Leucine

Methionine

Isoleucine

Tryptophan

Proline

Valine
Categories
Proline Biosynthesis Related Compounds
56-86-0 L-Glutamate
L-Glutamyl 5-phosphate
L-Glutamate 5-semialdehyde
70-26-8 L-Ornithine
(S)-1-Pyrroline-5-carboxylate
147-85-3 L-Proline

Proline and Derivatives:

Proline:

Derivatives: