Über die Konstitution des Bilirubins und über bilirubinoide Farbstoffe

Fischer, Hans; Plieninger, Hans; Weissbarth, Ottmar

doi:10.1515/bchm2.1941.268.5-6.197

Cited by 47 publications

(14 citation statements)

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“…The and suggests a helix-like conformation (Scheme 1,9) which brings rings A and D close together. Furthermore, while in the free acids l a and 2a the p-trans proton of the vinyl group in position 18 and 2, respectively, is distinctly deshielded by the amide carbonyl, no such effect is observed in the esters; obviously, the D-trans vinyl proton is in close proximity to the vicinal amide group only in the acid conformation.…”

Section: Spectroscopic Datamentioning

confidence: 99%

Chromatographic Separation and Spectroscopic Characterization of the Bilirubin Isomers IIIα, IXα, XIIIα and Their Dimethyl Esters

et al. 1982

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The three structural isomers bilirubin IXa (la), IIIa (2a), and XIIIa(3a) have been separated on a preparative scale by high-performance low-pressure liquid chromatography. They were converted into their dimethyl esters l b , 2b, and 3b and characterized by UV, IR, MS, and fully assigned 'H NMR data. NMR is the only spectroscopic method which makes it possible to analyze mixtures of the three isomeric dimethyl esters quantitatively. Chromatographische Trennung und spektroskopische Charakterisierung der Bilirubin-Isomeren IIIa, IXa und Xllla sowie ihrer DimethylesterDie drei Strukturisomeren Bilirubin IXa (la), IIIa (2a) und XIIIa (3a) wurden im praparativen MaRstab mittels hochaufldsender Niederdruckfliissigkeitschromatographie getrennt. AuRer UV-, IR-und MS-Daten von l a , 2 a und 3a und ihren Dimethylestern l b , 2b und 3b werden auch vollstandig zugeordnete 'H-NMR-Daten angegeben, die allein eine quantitative spektroskopische Analyse von Mischungen der isomeren Dimethylester erm0glichen.

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Section: Spectroscopic Datamentioning

confidence: 99%

Chromatographic Separation and Spectroscopic Characterization of the Bilirubin Isomers IIIα, IXα, XIIIα and Their Dimethyl Esters

et al. 1982

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“…It has been known since the work of Fischer and co-workers (Fischer, Plieninger & Weissbarth, 1941;Fischer & Plieninger, 1942) that bilirubin from human and animal sources is of the type IXoc (for a definition of the 52 conceivable isomers of bilirubin, see Fischer & Orth, 1937). Investigations as to the possible occurrence of isomers other than IXac have led to the conclusion that dog bile and commercial bilirubin contain such an isomer in very small proportions together with bilirubin IXcc (Petryka, 1966).…”

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confidence: 99%

Bilirubin conjugates of human bile. Nuclear-magnetic-resonance, infrared and optical spectra of model compounds

Kuenzle

1970

Biochemical Journal

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N.m.r., i.r. and optical spectra of model compounds were recorded. These were to help in elucidating the structures of the phenylazo derivatives of bilirubin conjugates isolated from human bile. Model compounds included commercial and human bile bilirubin, mesobilirubin, bilirubin dimethyl ester, dimethoxybilirubin dimethyl ester and the corresponding phenylazo derivatives. The phenylazo derivative of vinylneoxanthobilirubinic acid was also investigated. All compounds were of the type IXalpha, and no other isomer could be detected with the spectroscopic methods employed. The compounds crystallize as the lactams, except for dimethoxybilirubin dimethyl ester and its phenylazo derivative, which are held in the lactim ether configuration. With all other compounds no tautomeric forms other than the lactams could be detected, although small proportions of bilirubin must exist as the lactim. Bilirubin does not form a betaine, a structure that has been proposed by von Dobeneck & Brunner (1965) to explain the bathochromic shift of its optical spectrum as compared with the expected position of the absorption maximum at 420nm. However, this shift to 453nm can be explained on the basis of internal hydrogen bonds occurring between the carboxylic protons and the pyrrole rings of bilirubin, as proposed by Fog & Jellum (1963), and new evidence for such a bonding has been accumulated. The bilirubin sulphate described by Watson (1958), which is formed by treatment of bilirubin with concentrated sulphuric acid and acetic anhydride, was also investigated. The main product of this reaction was isolated as its phenylazo derivative, and was shown to be 3,18-di(ethylidene sulphate)-2,7,13,17-tetramethylbiladiene-ac-8,12-dipropionic acid. The reaction leading to this compound is an addition of sulphuric acid to the vinyl side chains of bilirubin according to Markownikoff's rule.

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“…ll 1,112 A drawback of this procedure is, however, the formation of a significant quantity of the 5(2H)-dipyrrylmethanone isomer of the desired 2,3-dihydro-l (1OH)-dipyrrinone (85), as a by-product, which is probably formed by double bond migration during cyclization of the levulinic acid chain of their common synthetic precursor. Some 2,3-dihydrobiliverdin derivatives have has been synthesized, as models for the chromophores of phycocyanin and phytochrome, taking advantage of the 81 facile base-catalyzed condensation of cc-pyrrolealdehydes with 3,3-dimethylpyrrolidin-2,4-dione (88). 113 Thus, reaction of the latter with 89 affords a 2,3-dihydro-4-oxo-l(10H)-dipyrrinone derivative (90) in 90% yield, which owing to intramolecular hydrogen bonding is exclusively obtained as the (E) isomer.…”

Section: Decahydro-l19-dioxo-21h-hilins)mentioning

confidence: 99%

Synthesis of Bilins

Gossauer

2003

The Porphyrin Handbook

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Über die Konstitution des Bilirubins und über bilirubinoide Farbstoffe

Cited by 47 publications

References 0 publications

Chromatographic Separation and Spectroscopic Characterization of the Bilirubin Isomers IIIα, IXα, XIIIα and Their Dimethyl Esters

Chromatographic Separation and Spectroscopic Characterization of the Bilirubin Isomers IIIα, IXα, XIIIα and Their Dimethyl Esters

Bilirubin conjugates of human bile. Nuclear-magnetic-resonance, infrared and optical spectra of model compounds

Synthesis of Bilins

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