Chemical modification of L-glutamine to alpha-amino glutarimide on autoclaving facilitates Agrobacterium infection of host and non-host plants: A new use of a known compound

When autoclaved at 121°C and 15 psi for 20 or 40 min, L-glutamine was structurally modified into 5-oxo proline and 3-amino glutarimide (α-amino glutarimide), respectively. Of the two autoclaved products, only α-amino glutarimide facilitated Agrobacterium infection of a number of resistant to susceptible plants. However, the compound did not have any vir gene inducing property.We report a one pot autoclave process for the synthesis of 5-oxo proline and α-amino glutarimide from L-glutamine. Xenobiotic detoxifying property of α-amino glutarimide is also proposed.Glutarimides are the hydrolyzed cyclic imides formed as a result of cyclization of glutamine. These compounds particularly, the α-amino glutarimides are important components of many extremely valuable drugs. The glutarimide moiety is present in a great number of molecules and has a broad spectrum of pharmacological activities. Many glutarimides have been reported to show notable anticancer activity, cytotoxicity against KB cells in vitro, and are also potent inhibitors of P388 murine leukemia in vivo [1]. Since aminoglutethimide inhibits steroidogenesis at the aromatase sites, it is used in treating metastatic breast cancer [2]. Antineoplaston A10 (N-[(3S)-2,6-dioxo-3-piperidyl]-2-phenyl-acetamide) is another glutarimide derivative, originally isolated from human urine. It has remarkable anticancer activity but lacks the toxicity of other common cancer drugs [3]. It has been suggested that A10 acts directly at the genomic level and alters the cellular responsiveness to steroidal hormones [4]. Thalidomides have special clinical value in a number of pathological conditions such as erythema nodosum leprosum, rheumatoid arthritis, HIV-associated oral ulcers, and chronic graft versus host diseases [5]. Both in vitro and in vivo studies have shown that thalidomides have the ability to inhibit tumor necrosis factor-α and its production [6]. FDA has approved this drug for the treatment of erythema nodosum leprosum (ENL