胆绿素和胆红素1 - O - 酰基 - β - D - 吡喃葡萄糖醛酸的合成。

Synthesis of biliverdin and bilirubin 1-O-acyl-beta-D-glucopyranuronic acids.

作者信息

Compernolle F

出版信息

Biochem J. 1980 Jun 1;187(3):857-62. doi: 10.1042/bj1870857.

DOI:10.1042/bj1870857

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1162472/

Abstract

Biliverdin and bilirubin mono- and di-beta-glucuronides were prepared by nucleophilic substitution of the 1-O-mesyl derivative of alpha-ethoxyethyl-protected glucuronic acid (compound II) with the tetrabutylammonium salts of biliverdin and bilirubin. Removal of the acetal-protecting groups by mild acid treatment yielded biliverdin glucuronides, which were reduced to bilirubin glucuronides. Depending on reaction conditions the pure beta-anomers or mixtures highly enriched in the beta-anomers were obtained. The biliverdin and bilirubin glucuronides were identical with pigments derived from bile. They were characterized as the IX alpha isomers and the beta-anomers by alkaline hydrolysis, n.m.r. spectroscopy, hydrolysis with beta-glucuronidase and conversion into dipyrrolic azopigments. Model reactions of the 1-O-mesylate (II) with other nucleophiles also were performed, i.e. the acetate anion and various alcohols.

摘要

通过用胆绿素和胆红素的四丁基铵盐对α-乙氧基乙基保护的葡萄糖醛酸（化合物II）的1-O-甲磺酰基衍生物进行亲核取代反应，制备了胆绿素和胆红素的单-β-葡萄糖醛酸苷和二-β-葡萄糖醛酸苷。通过温和的酸处理除去缩醛保护基团，得到胆绿素葡萄糖醛酸苷，将其还原为胆红素葡萄糖醛酸苷。根据反应条件，可以得到纯的β-异头物或高度富集β-异头物的混合物。胆绿素和胆红素葡萄糖醛酸苷与胆汁来源的色素相同。通过碱性水解、核磁共振光谱、β-葡萄糖醛酸酶水解以及转化为双吡咯偶氮色素，将它们表征为IXα异构体和β-异头物。还进行了1-O-甲磺酸酯（II）与其他亲核试剂的模型反应，即乙酸根阴离子和各种醇。

相似文献

1

Synthesis of biliverdin and bilirubin 1-O-acyl-beta-D-glucopyranuronic acids.胆绿素和胆红素1 - O - 酰基 - β - D - 吡喃葡萄糖醛酸的合成。

Biochem J. 1980 Jun 1;187(3):857-62. doi: 10.1042/bj1870857.

2

Synthesis, chromatographic purification, and analysis of isomers of biliverdin IX and bilirubin IX.胆红素IX异构体的合成、色谱纯化及分析。

Anal Biochem. 1991 Jun;195(2):273-8. doi: 10.1016/0003-2697(91)90329-r.

3

Preparation and properties of crystalline biliverdin IX alpha. Simple methods for preparing isomerically homogeneous biliverdin and [14C[biliverdin by using 2,3-dichloro-5,6-dicyanobenzoquinone.结晶型胆绿素IXα的制备及其性质。使用2,3-二氯-5,6-二氰基苯醌制备异构体均一的胆绿素和[14C]胆绿素的简单方法。

Biochem J. 1980 Aug 1;189(2):193-208. doi: 10.1042/bj1890193.

4

Rearranged glucuronic acid conjugates of bilirubin-IX alpha in post-obstructive bile. Structure elucidation of azopigments beta and gamma as ethyl anthranilate N-glycosides derived from 2-, 3- and 4-o-acyl glucuronides.梗阻性黄疸胆汁中胆红素-IXα的重排葡萄糖醛酸共轭物。偶氮色素β和γ作为源自2-、3-和4-O-酰基葡萄糖醛酸的邻氨基苯甲酸乙酯N-糖苷的结构解析。

Biomed Mass Spectrom. 1978 Jul;5(7):453-9. doi: 10.1002/bms.1200050707.

5

Glucuronic acid conjugates of bilirubin-IXalpha in normal bile compared with post-obstructive bile. Transformation of the 1-O-acylglucuronide into 2-, 3-, and 4-O-acylglucuronides.正常胆汁与梗阻后胆汁中胆红素-IXα的葡萄糖醛酸共轭物。1-O-酰基葡萄糖醛酸向2-、3-和4-O-酰基葡萄糖醛酸的转化。

Biochem J. 1978 Apr 1;171(1):185-201. doi: 10.1042/bj1710185.

6

Urinary excretion of isomers of biliverdin after destruction in vivo of haemoproteins and haemin.血蛋白和血红素在体内被破坏后胆绿素异构体的尿排泄情况。

Biochem J. 1985 Jul 15;229(2):477-83. doi: 10.1042/bj2290477.

7

Synthesis and separation by thin-layer chromatography of bilirubin-IX isomers. Their identification as tetrapyrroles and dipyrrolic ethyl anthranilate azo derivatives.胆红素-IX异构体的合成及薄层色谱分离。其作为四吡咯和二吡咯基邻氨基苯甲酸乙酯偶氮衍生物的鉴定。

Biochem J. 1976 May 1;155(2):405-17. doi: 10.1042/bj1550405.

8

Structure revision of disaccharidic conjugates of bilirubin-IX alpha in human bile and identification of phenylazo derivatives B4, B5, and B6 as 2-, 3- and 4-O-acylglucuronides.人胆汁中胆红素 -IXα 二糖缀合物的结构修订以及苯基偶氮衍生物 B4、B5 和 B6 作为 2 -、3 - 和 4 - O - 酰基葡萄糖醛酸苷的鉴定。

Biochem J. 1978 Dec 1;175(3):1095-101. doi: 10.1042/bj1751095.

9

The specificity of biliverdin reductase. The reduction of biliverdin XIII isomers.胆绿素还原酶的特异性。胆绿素 XIII 异构体的还原反应。

Biochim Biophys Acta. 1984 Jun 14;787(2):146-51. doi: 10.1016/0167-4838(84)90073-6.

10

Mass-spectrometric structure elucidation of dog bile azopigments as the acyl glycosides of glucopyranose and xylopyranose.犬胆汁偶氮色素作为吡喃葡萄糖和吡喃木糖的酰基糖苷的质谱结构解析

Biochem J. 1971 Dec;125(3):811-9. doi: 10.1042/bj1250811.

引用本文的文献

1

Potential bile acid metabolites. 24. An efficient synthesis of carboxyl-linked glucosides and their chemical properties.潜在的胆汁酸代谢物。24. 羧基连接的葡糖苷的高效合成及其化学性质。

Lipids. 2002 Jan;37(1):101-10. doi: 10.1007/s11745-002-0869-3.

本文引用的文献

1

Commercial bilirubin: A trinity of isomers.商业胆红素：异构体的三位一体。

FEBS Lett. 1971 Nov 1;18(2):315-317. doi: 10.1016/0014-5793(71)80475-1.

2

Determination of bilirubin glucuronide and assay of glucuronyltransferase with bilirubin as acceptor.胆红素葡萄糖醛酸苷的测定及以胆红素为受体的葡萄糖醛酸转移酶的测定。

Biochem J. 1968 Apr;107(4):507-18. doi: 10.1042/bj1070507.

3

Mass-spectrometric study of the azopigments obtained from bile pigments with diazotized ethyl anthranilate.用重氮化邻氨基苯甲酸乙酯从胆汁色素中获得的偶氮色素的质谱研究。

Biochem J. 1970 Dec;120(4):891-4. doi: 10.1042/bj1200891.

4

Separation by thin-layer chromatography and structure elucidation of bilirubin conjugates isolated from dog bile.从狗胆汁中分离出的胆红素共轭物的薄层色谱分离及结构解析。

Biochem J. 1975 Feb;145(2):185-99. doi: 10.1042/bj1450185.

5

Chemical synthesis of bilirubin glucuronide conjugates.胆红素葡萄糖醛酸共轭物的化学合成。

Biochim Biophys Acta. 1976 Nov 18;451(1):267-77. doi: 10.1016/0304-4165(76)90277-4.

6

Synthetic conjugates of bilirubin.胆红素的合成共轭物。

Biochem Soc Trans. 1976;4(2):303-4. doi: 10.1042/bst0040303.

7

The isolation and characterization of bilirubin diglucuronide, the major bilirubin conjugate in dog and human bile.狗和人胆汁中主要胆红素共轭物——胆红素双葡萄糖醛酸酯的分离与特性分析

Biochem J. 1976 Jun 1;155(3):477-86. doi: 10.1042/bj1550477.

8

Structure revision of disaccharidic conjugates of bilirubin-IX alpha in human bile and identification of phenylazo derivatives B4, B5, and B6 as 2-, 3- and 4-O-acylglucuronides.人胆汁中胆红素 -IXα 二糖缀合物的结构修订以及苯基偶氮衍生物 B4、B5 和 B6 作为 2 -、3 - 和 4 - O - 酰基葡萄糖醛酸苷的鉴定。

Biochem J. 1978 Dec 1;175(3):1095-101. doi: 10.1042/bj1751095.

9

Rearranged glucuronic acid conjugates of bilirubin-IX alpha in post-obstructive bile. Structure elucidation of azopigments beta and gamma as ethyl anthranilate N-glycosides derived from 2-, 3- and 4-o-acyl glucuronides.梗阻性黄疸胆汁中胆红素-IXα的重排葡萄糖醛酸共轭物。偶氮色素β和γ作为源自2-、3-和4-O-酰基葡萄糖醛酸的邻氨基苯甲酸乙酯N-糖苷的结构解析。

Biomed Mass Spectrom. 1978 Jul;5(7):453-9. doi: 10.1002/bms.1200050707.

10

Glucuronic acid conjugates of bilirubin-IXalpha in normal bile compared with post-obstructive bile. Transformation of the 1-O-acylglucuronide into 2-, 3-, and 4-O-acylglucuronides.正常胆汁与梗阻后胆汁中胆红素-IXα的葡萄糖醛酸共轭物。1-O-酰基葡萄糖醛酸向2-、3-和4-O-酰基葡萄糖醛酸的转化。

Biochem J. 1978 Apr 1;171(1):185-201. doi: 10.1042/bj1710185.

文献AI研究员

20分钟写一篇综述，助力文献阅读效率提升50倍。

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

文档翻译

学术文献翻译模型，支持多种主流文档格式。