Mass-spectrometric structure elucidation of dog bile azopigments as the acyl glycosides of glucopyranose and xylopyranose.

  title={Mass-spectrometric structure elucidation of dog bile azopigments as the acyl glycosides of glucopyranose and xylopyranose.},
  author={Frans Compernolle and Georg van Hees and Johan Fevery and Karel P. M. Heirwegh},
  journal={The Biochemical journal},
  volume={125 3},
1. The structures of the alpha(2)- and alpha(3)-azopigments, prepared by diazotization of dog bile with ethyl anthranilate, were shown by mass spectrometry and g.l.c. to correspond to azobilirubin beta-d-xylopyranoside and azobilirubin beta-d-glucopyranoside respectively. 2. Both azopigments consist of a mixture of two methyl vinyl isomers having structures (IIIa) and (IIIb) for the alpha(2)-azopigment and structures (IVa) and (IVb) for the alpha(3)-azopigment. Separation of methyl vinyl… Expand
23 Citations
Rearranged glucuronic acid conjugates of bilirubin‐IXα in post‐obstructive bile. Structure elucidation of azopigments β and γ as ethyl anthranilate N‐glycosides derived from 2‐, 3‐ and 4‐O‐acyl glucuronides
Azopigment analysis was performed on conjugates of bilirubin-IXalpha in bile of man and rats obtained after obstruction of the bile duct or in bile incubated under N2. The azopigments beta and gamma,Expand
Synthesis of biliverdin and bilirubin glucuronides
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Mass spectral study of derivatives of the four bilirubin-IX isomers.
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Chromatographic analysis and structure determination of biliverdins and bilirubins.
Since, in view of the lability and pronounced heterogeneity of bile Pigments, it is important to assess the composition and nature of chromatographically isolated pigments, the review is concluded by a brief evaluation of various structural tests. Expand
Glycosiduronic Acids and Related Compounds
Publisher Summary The chapter discusses later work on glycosiduronic acids and their derivatives from chemical point of view. As a consequence of the biological importance and general interest in theExpand
Plasma bile pigment conjugation modalities in icterus syndromes of various origin
It can be postulated that the synthesis of bilirubin diconjugates decreases both in hepatocellular and cholestatic jaundice, while monoglucuronidated as well as saccharide and glucoside conjugates increase. Expand
Comparative Studies on the Structures of Conjugated Bilirubin-IXα and Changes in Cholestasis
It is classically admitted that the major bile pigment resulting from heme catabolism in mammals is bilirubin-IXα (Lathe, 1972; Gray et al., 1972). The IIIα- and XIIIα-isomers that could arise fromExpand
Critique of the assay and significance of bilirubin conjugation.
This chapter describes the methodology and properties of uridine diphosphate (UDP)-glucuronyltransferase and of the related UDP-glycosyltransferase activities and delineates the applications to human disease. Expand
A polypeptide conjugate of bilirubin from human bile.
An alkali-stable bilirubin conjugate has been obtained from human T-tube bile as its phenylazo derivative, constituting the first biliprotein found in mammals. Expand
Enzymatic Conjugation and Insecticide Metabolism
Present knowledge concerning biochemical conjugations stemmed from the isolation and identification of conjugates from normal and pathological animal urine during the last century. As early as 1842,Expand