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大鼠体内1-卤代丙烷生成2-羟丙基硫醚氨酸的过程。

The formation of 2-hydroxypropylmercapturic acid from 1-halogenopropanes in the rat.

作者信息

Barnsley E A

出版信息

Biochem J. 1966 Aug;100(2):362-72. doi: 10.1042/bj1000362.

DOI:10.1042/bj1000362
PMID:5968536
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1265144/
Abstract
  1. 2-Hydroxypropylmercapturic acid, i.e. N-acetyl-S-(2-hydroxypropyl)-l-cysteine, has been isolated, as the dicyclohexylammonium salt, from the urine of rats dosed with 1-bromopropane. 2. The formation of the same metabolite from 1-chloropropane, 1-iodopropane, 1,2-epoxypropane and 1-chloropropan-2-ol has been demonstrated by chromatographic examination of the urine excreted by rats after they had been dosed with these compounds. 3. (+)- and (-)-Dicyclohexylammonium 2-hydroxypropylmercapturate have been prepared by fractional crystallization of the mixture of isomers obtained by two methods: the reaction of 1,2-epoxypropane with l-cysteine followed by acetylation, and the reduction of 2-oxopropylmercapturic acid. 4. The following compounds have also been prepared: S-(3-hydroxypropyl)-l-cysteine, (+)- and (-)-S-(2-hydroxypropyl)-l-cysteine, dicyclohexylammonium 3-hydroxypropylmercapturate, (+)- and (-)-dicyclohexylammonium 2-hydroxy-1-methylethylmercapturate, and (+)- and (-)-dicyclohexylammonium 1-(ethoxycarbonyl)ethylmercapturate.
摘要
  1. 2-羟丙基硫醚氨酸,即N-乙酰基-S-(2-羟丙基)-L-半胱氨酸,已作为二环己基铵盐从给1-溴丙烷的大鼠尿液中分离出来。2. 通过对给这些化合物的大鼠排出的尿液进行色谱检查,已证明1-氯丙烷、1-碘丙烷、1,2-环氧丙烷和1-氯丙醇-2能形成相同的代谢物。3. (+)-和(-)-二环己基铵2-羟丙基硫醚氨酸盐是通过两种方法得到的异构体混合物的分步结晶制备的:1,2-环氧丙烷与L-半胱氨酸反应后乙酰化,以及2-氧代丙基硫醚氨酸的还原。4. 还制备了以下化合物:S-(3-羟丙基)-L-半胱氨酸、(+)-和(-)-S-(2-羟丙基)-L-半胱氨酸、二环己基铵3-羟丙基硫醚氨酸盐、(+)-和(-)-二环己基铵2-羟基-1-甲基乙基硫醚氨酸盐,以及(+)-和(-)-二环己基铵1-(乙氧羰基)乙基硫醚氨酸盐。

相似文献

1
The formation of 2-hydroxypropylmercapturic acid from 1-halogenopropanes in the rat.大鼠体内1-卤代丙烷生成2-羟丙基硫醚氨酸的过程。
Biochem J. 1966 Aug;100(2):362-72. doi: 10.1042/bj1000362.
2
Biochemical studies of toxic agents. The metabolism of 1- and 2-bromopropane in rats.有毒物质的生化研究。大鼠体内1-溴丙烷和2-溴丙烷的代谢
Biochem J. 1966 Jul;100(1):282-8. doi: 10.1042/bj1000282.
3
Some metabolites of 1-bromobutane in the rabbit and the rat.1-溴丁烷在兔和大鼠体内的一些代谢产物。
Biochem J. 1968 Oct;109(5):727-36. doi: 10.1042/bj1090727.
4
Biochemical studies of toxic agents. The isolation of premercapturic acids from the urine of animals dosed with chlorobenzene and bromobenzene.有毒物质的生化研究。从用氯苯和溴苯给药的动物尿液中分离出前巯基尿酸。
Biochem J. 1968 Aug;109(1):143-7. doi: 10.1042/bj1090143.
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The metabolism of phenethyl bromide, styrene and styrene oxide in the rabbit and rat.苯乙基溴、苯乙烯和环氧苯乙烷在兔和大鼠体内的代谢
Biochem J. 1967 Sep;104(3):914-21. doi: 10.1042/bj1040914.
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Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein.由烯丙醇、烯丙酯和丙烯醛生物合成硫醚氨酸。
Biochem J. 1973 Aug;134(4):1093-1101. doi: 10.1042/bj1341093.
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The metabolism of S-methyl-L-cysteine.S-甲基-L-半胱氨酸的代谢
Biochem J. 1968 Mar;107(2):217-23. doi: 10.1042/bj1070217.
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Biochemical studies of toxic agents. 15. The biosynthesis of ethylmercapturic acid sulphoxide.有毒物质的生化研究。15. 乙硫基尿酸亚砜的生物合成。
Biochem J. 1964 Mar;90(3):588-96. doi: 10.1042/bj0900588.
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Reaction of mono-bromo derivatives of cyclopentane, cyclohexane and cycloheptane and of related compounds with glutathione in vivo and the nature of the sulphur-containing metabolites excreted.环戊烷、环己烷和环庚烷的单溴衍生物及相关化合物在体内与谷胱甘肽的反应以及排泄出的含硫代谢物的性质。
Biochem Pharmacol. 1971 Apr;20(4):897-907. doi: 10.1016/0006-2952(71)90052-9.
10
Stereo- and regioselective conjugation of S-halovinyl mercapturic acid sulfoxides by glutathione S-transferases.谷胱甘肽S-转移酶对S-卤代乙烯基硫醚氨酸亚砜的立体和区域选择性共轭作用。
Chem Res Toxicol. 1998 Jan;11(1):12-8. doi: 10.1021/tx970127a.

引用本文的文献

1
Some metabolites of 1-bromobutane in the rabbit and the rat.1-溴丁烷在兔和大鼠体内的一些代谢产物。
Biochem J. 1968 Oct;109(5):727-36. doi: 10.1042/bj1090727.
2
The metabolism of S-methyl-L-cysteine.S-甲基-L-半胱氨酸的代谢
Biochem J. 1968 Mar;107(2):217-23. doi: 10.1042/bj1070217.
3
Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein.由烯丙醇、烯丙酯和丙烯醛生物合成硫醚氨酸。
Biochem J. 1973 Aug;134(4):1093-1101. doi: 10.1042/bj1341093.
4
Dechloriation mechanisms of chlorinated olefins.氯化烯烃的脱氯机制
Environ Health Perspect. 1977 Dec;21:121-4. doi: 10.1289/ehp.7721121.

本文引用的文献

1
BIOCHEMICAL STUDIES OF TOXIC AGENTS. THE METABOLISM OF IODOMETHANE.有毒物质的生化研究。碘甲烷的代谢
Biochem J. 1965 Apr;95(1):77-81. doi: 10.1042/bj0950077.
2
Biochemical studies of toxic agents. 14. The biosynthesis of ethylmercapturic acid.有毒物质的生化研究。14. 乙硫基尿酸的生物合成。
Biochem J. 1963 Jan;86(1):145-52. doi: 10.1042/bj0860145.
3
Biochemical studies on toxic agents. 12. The biosynthesis of n-propylmercapturic acid from n-propyl halides.有毒物质的生化研究。12. 由正丙基卤化物生物合成正丙基硫醚氨酸。
Biochem J. 1960 Apr;75(1):28-33. doi: 10.1042/bj0750028.
4
Biochemical studies of toxic agents. The metabolism of 1- and 2-bromopropane in rats.有毒物质的生化研究。大鼠体内1-溴丙烷和2-溴丙烷的代谢
Biochem J. 1966 Jul;100(1):282-8. doi: 10.1042/bj1000282.
5
Biochemical studies of toxic agents. 15. The biosynthesis of ethylmercapturic acid sulphoxide.有毒物质的生化研究。15. 乙硫基尿酸亚砜的生物合成。
Biochem J. 1964 Mar;90(3):588-96. doi: 10.1042/bj0900588.
6
Formation of mercapturic acids. 5. Metabolism of some halogenoparaffins and nitroparaffins.硫醚氨酸的形成。5. 某些卤代烷烃和硝基烷烃的代谢。
Biochem J. 1964 Jan;90(1):127-32. doi: 10.1042/bj0900127.