Isolation of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-thiolactic acid, a new metabolite of histidine, from normal human urine and its formation from S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine.
Isolation of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-thiolactic acid, a new metabolite of histidine, from normal human urine and its formation from S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine.
复制标题
从正常人尿液中分离 S-[2-羧基-1-(1H-咪唑-4-基)乙基]-3-硫代乳酸（组氨酸的新代谢物）及其从 S-[2-羧基-1 的形成
DOI：
10.1042/bj2970475
复制
发表时间：
1994
期刊：
影响因子：
--
通讯作者：
H. Shimizu
中科院分区：
文献类型：
--
作者：
M. Kinuta;T. Ubuka;W. Yao;Y. ;H. Shimizu
S-[2-羧基-1-（1h -咪唑-4-基）乙基]-3-硫代乳酸（CIE-TL）是一种具有含硫侧链的新型咪唑类化合物，采用离子交换柱色谱法从人尿中分离得到，并通过质谱、红外分光光度、高压纸电泳、元素分析和化学合成等理化分析对其进行了表征。以S-[2-羧基-1-（1h -咪唑-4-基）乙基]半胱氨酸（CIE-Cys）与NaNO2在盐酸中反应合成了CIE-TL。大鼠肝脏或肾脏均质液在磷酸盐缓冲液中酶降解CIE-Cys时也会形成CIE-TL，可能是通过代谢中间体S-[2-羧基-1-（1h -咪唑-4-基）乙基]-3-硫代嘌呤酸形成的，这伴随着3-[（羧甲基）硫]-3-（1h -咪唑-4-基）丙酸的形成，这是一种以前在人类尿液中发现的化合物[Kinuta， Yao, Masuoka, Ohta， Teraoka和Ubuka (1991) Biochem]。[j].科学通报，1999,16(2):1 -6。这些结果表明CIE-Cys [Kinuta， Ubuka, Yao, Futani, Fujiwara and Kurozumi (1992) Biochem.][j][283,39 -40]是尿液化合物的生理前体，l -组氨酸的部分代谢途径是由天然硫醇化合物如半胱氨酸和谷胱甘肽内聚到尿酸（组氨酸的第一个分解代谢物）引发的。
S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]-3-thiolactic acid (CIE-TL), a novel imidazole compound with a sulphur-containing side chain, was isolated from normal human urine by ion-exchange column chromatography, and characterized by physicochemical analyses involving m.s., i.r. spectrophotometry, high-voltage paper electrophoresis and elemental analysis as well as chemical synthesis. CIE-TL was synthesized by the reaction of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine (CIE-Cys) with NaNO2 in HCl. CIE-TL was also formed during enzymic degradation of CIE-Cys by rat liver or kidney homogenate in a phosphate buffer, possibly via the metabolic intermediate S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-thiopyruvic acid, and this was accompanied by the formation of 3-[(carboxymethyl)thio]-3-(1H-imidazol-4-yl)propanoic acid, a compound previously found in human urine [Kinuta, Yao, Masuoka, Ohta, Teraoka and Ubuka (1991) Biochem. J. 275, 617-621]. These results suggest that CIE-Cys [Kinuta, Ubuka, Yao, Futani, Fujiwara and Kurozumi (1992) Biochem. J. 283, 39-40] is a physiological precursor of the urinary compounds and that L-histidine is metabolized in part via an alternative pathway initiated by the adduction of natural thiol compounds such as cysteine and GSH to urocanic acid, the first catabolite of histidine.