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- W2008243929 abstract "A symmetrical C(10)-thiabilirubin analogue, 8,12-bis(2-carboxyethyl)-2,3,17,18-tetraethyl-7,13-dimethyl-10-thia-(21H,23H,24H)-bilin-1,19-dione (1), was synthesized from 8-(2-carboxyethyl)-2,3-diethyl-7-methyl-10H-dipyrrin-1-one in one step by reaction with sulfur dichloride. The thia-rubin exhibited the expected IR, UV−vis, and NMR spectroscopic properties, which are rather similar to those of mesobilirubin-XIIIα. Like bilirubin and mesobilirubin, 1 adopts an intramolecularly hydrogen-bonded conformation, shaped like a ridge-tile but with a steeper pitch. The longer C−S bond lengths and smaller bond angles at C−S−C, as compared to C−CH2−C, lead to an interplanar angle between the two dipyrrinones of only 74°or considerably less than that of bilirubin (∼100°). On normal- and reversed-phase chromatography, 1 is substantially less polar than bilirubin. Despite this conformational distortion, 1 is metabolized in normal rats to acyl glucuronides, which are secreted into bile. In mutant (Gunn) rats lacking bilirubin glucuronosyl transferase, 1 (like bilirubin) was not excreted in bile." @default.
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- W2008243929 date "2001-02-13" @default.
- W2008243929 modified "2023-09-25" @default.
- W2008243929 title "Synthesis and Metabolism of the First Thia-Bilirubin" @default.
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- W2008243929 doi "https://doi.org/10.1021/jo001598w" @default.
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