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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

Indra Sandal1, Amita Bhattacharya4*, Uksha Saini2, Devinder Kaur4, Shveta Sharma4, Ashu Gulati4, Jonnala K Kumar3, Neeraj Kumar4, Jyotsna Dayma4, Pralay Das4, Bikram Singh4 and Paramvir S Ahuja4

Author Affiliations

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

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BMC Chemical Biology 2011, 11:1  doi:10.1186/1472-6769-11-1

Published: 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.