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• W1495755013 abstract "Abstract 1. Seven unusual compounds were detected in large amounts in urine from rats treated with hypoglycin A (l-α-amino-β-(methylenecyclopropyl)propionic acid). They were isolated by a combination of preparative gas-liquid chromatography and silver nitrate-impregnated thin layer chromatography. From evidence obtained by nuclear magnetic resonance, mass and infrared spectrometry, and chemical techniques, these compounds were identified as cis-4-decene-1,10-dioic, cis,cis-4,7-decadiene-1,10-dioic, cis-4-octene-1,8-dioic, glutaric, and adipic acids, N-isovalerylglycine, and N-(methylenecyclopropyl)acetylglycine. The amounts of these compounds found in urine of hypoglycin treated rats were 50 to several hundred times of controls. These compounds were not accumulated in urine of rats treated with 4-pentenoic acid, which has been believed to act similarly to hypoglycin A. 2. In vivo and in vitro experiments suggest that accumulation of glutarate is due to inhibition of glutaryl coenzyme A dehydrogenase. 3. N-(Methylenecyclopropyl)acetylglycine appears to be one of the major final metabolites of hypoglycin A. Hypoglycin A is metabolized to (methylenecyclopropyl)acetyl-CoA which is not oxidized further but is mostly conjugated and excreted in urine. N-(Methylenecyclopropyl)acetylglycine accounts for about 25 to 40% of such conjugates. 4. Excretion of N-isovalerylglycine is consistent with the inhibition of isovaleryl-CoA dehydrogenase by hypoglycin A. 5. To identify precursors of 4-decenedioate and 4-octenedioate, experiments were carried out using [U-14C]oleate as a substrate on the assumption that these compounds were the products of ω oxidation and subsequent bilateral β oxidation of oleate. However, this hypothesis could not be confirmed. Further 14C from [U-14C]palmitate was not incorporated into adipate in a significant amount." @default.
• W1495755013 created "2016-06-24" @default.
• W1495755013 creator A5036683171 @default.
• W1495755013 date "1972-12-01" @default.
• W1495755013 modified "2023-09-28" @default.
• W1495755013 title "On the Mode of Action of Hypoglycin A" @default.
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• W1495755013 doi "https://doi.org/10.1016/s0021-9258(19)44549-3" @default.
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