azaserine

Azaserine is a **naturally occurring serine derivative diazo compound** with **antineoplastic** (anti-cancer), **antibiotic**, and **antifungal** properties. It acts primarily as a **purine antagonist** and as a **structural analogue of glutamine**, competitively inhibiting glutamine-dependent enzymatic activities—most notably **glutamine amidotransferase**, a key enzyme in purine biosynthesis and the metabolic hexosamine pathway. Azaserine **inhibits the rate-limiting step of the hexosamine biosynthesis pathway** and **irreversibly inhibits gamma-Glutamyltranspeptidase (GGT1)** by direct interaction at the substrate-binding pocket. It also dampens purine biosynthesis by reacting with cysteine residues in enzyme active sites, and induces DNA damage via formation of carboxymethylated bases and O6-methylguanine. It has been studied as a potential antineoplastic agent, but is not an approved or widely used pharmaceutical. Azaserine is isolated from Streptomyces species[1][2][3][5][8].

Other names

O-diazoacetyl-L-serine