Biliverdin IX α, Intermediate and End Product of Tetrapyrolle Biosynthesis

Köst, Hans‐Peter; Benedikt, Eva

doi:10.1515/znc-1982-11-1202

Cited by 10 publications

(1 citation statement)

References 36 publications

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“…1-9). As side chains or 1&carbon ring substituents, all bile pigments described thus far have four methyl groups, two propionic acid groups, and two vinyl groups, one or both of which can be isomerized to ethylidene (4, 10, 11) or reduced to ethyl (6,10,11). These substituents are arranged in the sequence found in protoporphyrin IX; in fact, all these bile pigments are formed from protoheme (8,(12)(13)(14), whose oxidative breakdown to biliverdin is catalyzed by the enzyme heme oxygenase (15-17).…”

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confidence: 99%

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Brumm¹,

Fried²,

Friedmann³

1983

Proc. Natl. Acad. Sci. U.S.A.

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A blue bile pigment, possessing four acetic and four propionic acid side chains has been isolated from extracts of the anaerobic microorganism Clostridium tetanomorphum and in smaller amounts from Propionibacterium shermanii. The compound could be prepared in larger amounts by incubation of C. tetanomorphum enzyme extracts with added 8-aminolevulinic acid. The ultraviolet-visible, infrared, and proton magnetic resonance spectra of the pigment indicate a chromophore of the biliverdin type. Field-desorption mass spectrometry of the purified methyl ester showed a strong molecular ion at m/e = 962. This corresponds to the molecular weight expected for the octamethyl ester of a bilatriene type of bile pigment structurally derived from uroporphyrin 1m or I. Of the five possible structures, two could be eliminated by proton magnetic resonance spectroscopy. The name bactobilin is proposed for this previously unreported bile pigment.The open-chain tetrapyrrole compounds known as bile pigments are widely distributed. They are found free or bound to protein in mammals, birds, amphibians, reptiles, fish, molluscs, and insects and in algae and higher plants (for reviews, see refs. 1-9). As side chains or 1&carbon ring substituents, all bile pigments described thus far have four methyl groups, two propionic acid groups, and two vinyl groups, one or both of which can be isomerized to ethylidene (4, 10, 11) or reduced to ethyl (6,10,11). These substituents are arranged in the sequence found in protoporphyrin IX; in fact, all these bile pigments are formed from protoheme (8,(12)(13)(14), whose oxidative breakdown to biliverdin is catalyzed by the enzyme heme oxygenase (15-17). Bile pigments thus far have not been detected in prokaryotes. The present paper reports the isolation and in vitro formation of a bile pigment from the bacterium Clostridium tetanomorphum. This anaerobic organism makes uroporphyrinogen, the precursor of vitamin B-12, but not heme, protoporphyrinogen, or coproporphyrinogen. The isolated bile pigment is of interest not only because of its detection in a prokaryote, but also because its 13-carbon ring substituents, four acetic acid and four propionic acid groups, correspond to those of a uroporphyrin and not of protoporphyrin. MATERIALS AND METHODSSupplies. -Aminolevulinic acid was obtained from Sigma;biliverdin IXa dimethyl ester and the fully esterified methyl esters of uroporphyrin III, coproporphyrin III, protoporphyrin IX, and heptacarboxylporphyrin I, were from Porphyrin Products (Logan, UT). The n-hexane used for flash chromatography was "95 + %" (Aldrich), whereas the n-hexane for thin-layer chromatography was 99 mol % pure (Fisher). Other chemicals used were reagent grade or better. Silica gel for flash chromatography and a flash chromatography column, 3.4-cm diameter, were obtained from J. T. Baker. Whatman high-performance silica thin-layer chromatography plates with a preadsorbent spotting area (type LHP-K, 10 x 20 cm) and E. Merck precoated cellulose thin-layer chromatography plates were...

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mentioning

confidence: 99%

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Brumm¹,

Fried²,

Friedmann³

1983

Proc. Natl. Acad. Sci. U.S.A.

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Syntheses of Bile Pigments. Part 16. Synthesis of a vinyl‐substituted 2,3‐Dihydrobilinedione: Possible role of this new class of bile pigments in phycobilin biosynthesis

Gossauer

Nydegger

Benedikt³

et al. 1989

Helvetica Chimica Acta

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The total synthesis of racemic cis-2,3,18',18*-tetrahydroprotobiliverdin I X a dimethyl ester (19b), which is identical with the dimethyl ester of rac-4, is described (Scheme 2). Under virtually neutral conditions, in solution, this bile pigment isomerized within a few min to racemic Z-phycocyanobilin dimethyl ester (rue-5b). Likewise, acid-catalyzed ally1 rearrangement of 3-vinyl-substituted cis-and trans-2,3-dihydrodipyrrin-1 (10H)-ones l l c and 13c, respectively, yielded the corresponding ethylidene derivatives. In this case, however, the E-isomer was formed stereoselectively from both substrates. The above results prove that, if protobiliverdin

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A comprehensive bibliography to the world’s literature on the algal genus Cyanidium Geitler 1933 including its ecological cohorts Galdieria Merola in Merola et al. 1981 and Cyanidioschizon De Luca, Taddei and Varano 1978 with indexing to the major areas of biological interest

Ott¹,

Petrik-Ott²

1994

Evolutionary Pathways and Enigmatic Algae: Cyanidium Caldarium (Rhodophyta) and Related Cells

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Biliverdin IX α, Intermediate and End Product of Tetrapyrolle Biosynthesis

Cited by 10 publications

References 36 publications

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Syntheses of Bile Pigments. Part 16. Synthesis of a vinyl‐substituted 2,3‐Dihydrobilinedione: Possible role of this new class of bile pigments in phycobilin biosynthesis

A comprehensive bibliography to the world’s literature on the algal genus Cyanidium Geitler 1933 including its ecological cohorts Galdieria Merola in Merola et al. 1981 and Cyanidioschizon De Luca, Taddei and Varano 1978 with indexing to the major areas of biological interest

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