aminooxyacetic

Aminooxyacetic acid is a small organic compound used as a biochemical tool and reagent. Its structure comprises a carboxyl group attached to a two-carbon chain that bears an aminooxy substituent (-ONH2), giving the formula C2H5NO3 and typically represented as HOOC-CH2-ONH2. The molecule is polar and water-soluble, and it can be used in various salt forms for solubility and handling.

In biochemistry, aminooxyacetic acid functions as a broad-spectrum inhibitor of pyridoxal phosphate (PLP)-dependent enzymes. It acts by forming an external aldimine with the PLP cofactor within enzyme active sites, thereby inhibiting catalysis of many PLP-dependent reactions, including transaminases and other PLP-dependent enzymes. Because of this mode of action, AOAA is widely employed as a pharmacological tool to study amino acid metabolism, enzyme mechanisms, and the roles of PLP-dependent enzymes in cellular processes. In vitro, it is typically used at millimolar concentrations, and in vivo interpretations require caution due to limited enzyme selectivity.

In chemical biology, the aminooxy group provides a functional handle for oxime ligation. Aminooxyacetic acid can serve as a linker or reagent for conjugating aldehyde- or ketone-containing biomolecules under mild conditions, enabling labeling, tagging, or immobilization in diverse applications.

Safety and handling follow standard laboratory practices for small organic acids and aminooxy compounds. Handle with appropriate protective equipment and consult safety data resources for specific hazard information.