
doi: 10.1021/jf60190a045
pmid: 4755823
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
Chemistry, Chemical Phenomena, Atrazine, Chromatography, Thin Layer, Plants, Glutathione
Chemistry, Chemical Phenomena, Atrazine, Chromatography, Thin Layer, Plants, Glutathione
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