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Enzymatic Studies on the Metabolism of the Tetrahydrofurfuryl Mercaptan Moiety of Thiamine Tetrahydrofurfuryl Disulfide:III. Oxidative Cleavage of the Tetrahydrofuran Moiety
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- FUJITA Takeshi
- Biological Research Laboratories, Central Researche Division, Takeda Chem. Ind., Ltd.
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- SUZUOKI Ziro
- Biological Research Laboratories, Central Researche Division, Takeda Chem. Ind., Ltd.
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Description
In vitro metabolism of the tetrahydrofuran ring was studied using [35S]methyl tetrahydrofurfuryl sulfone as a substrate with rat liver homogenates. The tetrahydrofuran ring was first hydroxylated by liver microsomes in the presence of NADPH and O2. The reaction product was isolated and identified as methyl 5-hydroxytetrahydrofurfuryl sulfone by instrumental analyses of the infrared, nuclear magnetic resonance, and mass spectra. An NADH-generating system could not support this microsomal hydroxylation, and the involvement of a peroxidative reaction was excluded. Methyl 5-hydroxytetrahydrofurfuryl sulfone thus formed was further oxidized to 4-hydroxy-5-methylsulfonylvaleric acid by incubation with the hepatic cytosol. Microsomes were no longer necessary for the second reaction. These results indicated that the tetrahydrofuran ring was first hydroxylated at the 5-position by microsomes and further cleaved to the straight-chain fatty acid via the intermediate formation of either an aldehyde form or a γ-lactone in the presence of cytosol.
Journal
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- J Biochem (Tokyo)
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J Biochem (Tokyo) 74 (4), 733-738, 1973
The Japanese Biochemical Society
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Details 詳細情報について
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- CRID
- 1574231877870538368
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- NII Article ID
- 130003539170
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- ISSN
- 0021924X
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- Text Lang
- en
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- Data Source
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- CiNii Articles