胆汁色素的制备与表征
The preparation and characterization of bile pigments.
作者信息
Stoll M S, Gray C H
出版信息
Biochem J. 1977 Apr 1;163(1):59-101. doi: 10.1042/bj1630059.
Abstract
Brief reduction of bilirubin with dilute sodium amalgam was shown to give chromogens containing both vinyl and ethylidene beta-substituents. Acid-catalysed rearrangement of these chromogens with bilirubin or mesobilirubin and subsequent dehydrogenation gave a range of new violins containing unconjugated ethylidene and vinyl substitutents. Rearrangements between mesobilirubinogen, bilirubin and mesobilirubin gave dihydrobiliviolins, mesobiliviolins, biliverdins, dihydrobiliverdins and mesobiliverdins of the IIIalpha, IXalpha and XIIIalpha series. In this way 30 compounds were prepared, purified by t.l.c. as dimethyl esters, and characterized by n.m.r., mass and electronic spectroscopy, and by chemical interconversion and degradation.
摘要
结果表明，用稀钠汞齐短暂还原胆红素可得到同时含有乙烯基和亚乙基β-取代基的色原。这些色原与胆红素或中胆红素经酸催化重排，随后脱氢，得到一系列含有未共轭亚乙基和乙烯基取代基的新紫红素。中胆素原、胆红素和中胆红素之间的重排产生了IIIα、IXα和XIIIα系列的二氢胆红素紫红素、中胆红素紫红素、胆绿素、二氢胆绿素和中胆绿素。通过这种方法制备了30种化合物，通过薄层层析作为二甲基酯进行纯化，并通过核磁共振、质谱和电子光谱以及化学相互转化和降解进行表征。
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本文引用的文献
1
A study of the reported occurrence of mesobilirubin in human bile.
Proc Soc Exp Biol Med. 1963 Mar;112:756-8. doi: 10.3181/00379727-112-28161.
2
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.
3
Structure of phycoerythrobilin and phycocyanobilin.藻红胆素和藻蓝胆素的结构。
Nature. 1967 Sep 30;215(5109):1477-8. doi: 10.1038/2151477a0.
4
A new method of interpretation of the ferric chloride oxidation patterns of the urobilinoids.一种尿胆素原类化合物氯化铁氧化模式的新解释方法。
Arch Biochem Biophys. 1969 May;131(2):414-22. doi: 10.1016/0003-9861(69)90413-5.
5
Separation and identification of biliverdin isomers and isomer analysis of phycobilins and bilirubin.
J Chromatogr. 1970 Aug 12;50(3):458-68. doi: 10.1016/s0021-9673(00)97973-1.
6
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7
[Degradation of bile pigments with chromic acid and chromate].[胆汁色素用铬酸和铬酸盐的降解]
Hoppe Seylers Z Physiol Chem. 1969 Nov;350(11):1291-300.
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