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
- Equal contributors
1 Center for Molecular Medicine and Infectious Diseases, Department of Biomedical Sciences and Pathobiology, Virginia Tech, Blacksburg, VA-24061, USA
2 Department of Biotechnology, College of Life Sciences, Bowling Green State University, Bowling Green, Ohio, USA
3 Central Institute of Medicinal and Aromatic Plants, Resource Centre, Boduppal, Hyderabad 500039 (A.P.), India
4 CSIR-Institute of Himalayan Bioresource Technology, Council of Scientific and Industrial Research, Palampur-176061, H. P. India
BMC Chemical Biology 2011, 11:1 doi:10.1186/1472-6769-11-1Published: 31 May 2011
Accidental autoclaving of L-glutamine was found to facilitate the Agrobacterium infection of a non host plant like tea in an earlier study. In the present communication, we elucidate the structural changes in L-glutamine due to autoclaving and also confirm the role of heat transformed L-glutamine in Agrobacterium mediated genetic transformation of host/non host plants.
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.