5-Aminovaleric acid

5-Aminovaleric acid is an organic compound with the formula C₅H₁₁NO₂. It is a derivative of valeric acid with an amino group at the 5-position. This compound is of interest in the field of biochemistry and organic chemistry due to its role as an intermediate in the biosynthesis of various biologically active molecules.

Structure and Properties

5-Aminovaleric acid is a straight-chain amino acid with a carboxylic acid group (–COOH) and an amino group (–NH₂) attached to a five-carbon aliphatic chain. Its IUPAC name is 5-aminopentanoic acid. The presence of both an amino group and a carboxylic acid group makes it a zwitterion at physiological pH, where the amino group is protonated (–NH₃⁺) and the carboxylic acid group is deprotonated (–COO⁻).

Synthesis

5-Aminovaleric acid can be synthesized through several methods:

• Chemical Synthesis: It can be produced by the reduction of 5-nitrovaleric acid or by the hydrolysis of 5-cyanovaleric acid.
• Biological Synthesis: It is also produced biologically as an intermediate in the degradation of lysine via the saccharopine pathway.

Biological Role

In biological systems, 5-aminovaleric acid is involved in the catabolism of lysine. It is converted into 5-aminovalerate, which is further metabolized into succinyl-CoA, entering the tricarboxylic acid cycle (TCA cycle) for energy production.

Applications

5-Aminovaleric acid is used in research as a precursor for the synthesis of various pharmaceuticals and biopolymers. It is also studied for its potential use in the production of biodegradable plastics and as a building block for nylon-type polymers.

Safety and Handling

As with many chemical compounds, proper safety precautions should be taken when handling 5-aminovaleric acid. It should be stored in a cool, dry place, and contact with skin and eyes should be avoided. Safety data sheets (SDS) provide detailed information on handling and potential hazards.

Also see

• Valeric acid
• Amino acids
• Lysine degradation
• Biodegradable plastics