Atrazine metabolism in sorghum. Catabolism of the glutathione conjugate of atrazine

Lamoureux, G.L. and Stafford, L.E. and Shimabukuro, R.H. and Zaylskie, R.G. (1973) Atrazine metabolism in sorghum. Catabolism of the glutathione conjugate of atrazine. Journal of Agricultural and Food Chemistry, 21 (6). pp. 1020-1030.

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The major pathway of atrazine metabolism in intact sorghum was shown to involve the following steps: atrazine 'right arrow' S-(4-ethylamino-6-isopropylamino-1,3,5-triazin-2-yl)glutathione 'right arrow' gamma -glutamyl-S-(4-ethylamino-6-isopropylamino-1,3,5-triazin-2-yl)cysteine 'right arrow' S-(4-ethylamino-6-isopropylamino-1,3,5-triazin-2-yl cysteine 'right arrow' N-(4-ethylamino-6-isopropylamino-1,3,5-triazin-2-yl)cysteine 'right arrow' N-(4-ethylamino-6-isopropylamino-1,3,5-triazin-2-yl)lanthionine. From 40 to 87% of the atrazine entering sorghum through the roots was estimated to be metabolized via this pathway. Evidence indicated that atrazine can also be metabolized via this route after first undergoing N-dealkylation. The step involving conversion from the S- to the N-cysteine conjugate was shown to be a non-enzymatic rearrangement. This is the first reported occurrence of S-(4-ethylamino-6-isopropylamino-1,3,5-triazin-2-yl)cysteine, the lanthionine conjugate, 2-hydroxy-4-amino-6-isopropylamino-1,3,5-triazine and 2-hydroxy-4,6-diamino-1,3,5-triazine (ammeline) in sorghum. Structural formulae for these compounds and the metabolic pathway are shown. From summary

Item Type: Article
Author Affiliation: USDA, ARS., Metabolism and Radiation Research Laboratory, Fargo, N. Dakota, 58102, USA.
Subjects: Crop Improvement
Plant Physiology and Biochemistry > Biochemistry
Divisions: Sorghum
Depositing User: Mr. SanatKumar Behera
Date Deposited: 23 May 2012 10:18
Last Modified: 23 May 2012 10:19
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