493-89-0

Upstream product

• 635-65-4 bilirubin 
• 69853-44-7 bilirubin 
• 635-65-4 bilirubin IXα 
• 19792-68-8 bilirubin dimethylester 
• 10035-62-8 α-biliverdin-IX dimethyl ester 

Downstream Products

• 97241-04-8 C₅₃H₅₆N₆O₈ 
• 109203-65-8 biliverdin-IXα bis<(S)-proline benzyl ester> 
• 97241-10-6 C₅₁H₅₆N₆O₄ 
• 109203-61-4 biliverdin-IXα bis<(S)-phenylalanine t-butyl ester> 
• 10035-62-8 α-biliverdin-IX dimethyl ester 
• 20189-42-8 3-ethyl-4-methyl-pyrrole-2,5-dione 

Relevant academic research and scientific papers

A method for preparing high-content bilirubin IX[alpha] from bilirubin IX[alpha] diester

A method for preparing high-content bilirubin IX[alpha] from bilirubin IX[alpha] diester is disclosed, belonging to the field of bilirubin IX[alpha] preparation. The method includes following steps (aroute including firstly hydrolysis and then reduction): a step of adding dropwise a methanol solution of sodium hydroxide into an alcohol solution of bilirubin IX[alpha] diester, adding water, then performing hydrolysis, adjusting pH to 4-5 with a weak acid, performing rotary evaporation to remove a solvent, washing a product with water to remove inorganic salt, and performing vacuum drying to obtain bilirubin IX[alpha]; and a step of adding a free radical scavenger (stabilizer) into an alcohol solution of the bilirubin IX[alpha], adding a reductant that is borohydride, adding an acetone immediately after reduction is finished to decompose the excessive reductant, then adjusting pH to 4-5 with weak acid, performing rotary evaporation to remove a solvent, performing water washing, and performing purification with methanol and chloroform to obtain bilirubin IX[alpha] the purity of which is more than 97%. The method has characteristics of no need of chromatographic separation, mild reaction conditions, low cost, and convenient operation, and is suitable for industrial large-scale production.

Bilirubin oxidase from Magnaporthe oryzae and applications thereof

The present invention relates to a novel bilirubin oxidase from Magnaporthe oryzae, to the method of preparation thereof as well as use thereof notably for assay of bilirubin and for the application of enzymatic biofuel cells.

Biliverdin amides reveal roles for propionate side chains in bilin reductase recognition and in holophytochrome assembly and photoconversion

Linear tetrapyrroles (bilins) perform important antioxidant and light-harvesting functions in cells from bacteria to humans. To explore the role of the propionate moieties in bilin metabolism, we report the semisynthesis of mono- and diamides of biliverdin IXα and those of its non-natural XIIIα isomer. Initially, these were examined as substrates of two types of NADPH-dependent biliverdin reductase, BVR and BvdR, and of the representative ferredoxin-dependent bilin reductase, phycocyanobilin:ferredoxin oxidoreductase (PcyA). Our studies indicate that the NADPH-dependent biliverdin reductases are less accommodating to amidation of the propionic acid side chains of biliverdin IXα than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides were also assembled with BV-type and phytobilin-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native Pr dark states of these biliprotein photosensors. Neither ionizable propionate side chain proved to be essential to primary photoisomerization for both classes of phytochromes, but an unsubstituted 12-propionate was required for full photointerconversion of phytobilin-type phytochrome Cph1. Taken together, these studies provide insight into the roles of the ionizable propionate side chains in substrate discrimination by two bilin reductase families while further underscoring the mechanistic differences between the photoconversions of BV-type and phytobilin-type phytochromes.

Urinary excretion of α- and β-isomers of biliverdin-IX in humans

The distribution and relative proportions of the four isomers of α-, β-, γ- and δ-biliverdin-IX were investigated using urinary samples from seven healthy adults. The biliverdins from samples were adsorbed on talc, and the adsorbed biliverdins were then soaked in a solution of methanol and concentrated sulfuric acid for derivation to the dimethyl esters. The esters were passed to a reversed-phase cartridge for clean-up, then quantitated by HPLC on a reversed-phase column. The analyses revealed that the biliverdins in 24-h urine were comprised of 6.4 ± 2.5 nmol α- and 9.3 ± 5.4 nmol β-isomers. The HPLC analyses suggested the presence of a δ-isomer in a much smaller amount, but no γ-isomer was detected. The identifications of α- and β-isomers were performed with co-chromatography and absorption spectra.

Reactivity of Pyrrole Pigments, Part 15: On the Oxidation of Bilirubins and Biliverdins

Characteristic oxidation reactions of bilin-1,19-diones (biliverdins) and biladien-ac-1,19-diones (bilirubins) were reinvestigated.These include bromine and iodine oxidation of biliverdin IXα, bilirubin IXα and their Zn(II)complexes, the reaction described by Siedel (1941) of mesobilirubin XIIIα dimethyl ester with nitric acid (Gmelin reaction) and Smith's oxidation (1977) of etiobiliverdin IVγ using Tl triacetate and Pb tetra-acetate.For some of these reaction products new structures were assigned on the basis of their spectrometric data.These structures agreed with the expected reactivity pattern of biliverdins and bilirubins. Keywords: Bilipurpurins; Biliviolins; Electron transfer vs.Electrophilic attack.

On the Fate of Biliverdin-IIIα-dimethyl Ester Formed by Scrambling During Syntheses of Biliverdin-IXα-dimethyl Ester from Bilirubin

In the preparations of biliverdin-IXα-dimethyl ester (2b) from bilirubin-IXα (1) the ratio of the XIIIα- and IIIα-isomers 3b and 4b, formed via intermolecular scrambling, should be unity.However, irrespective of the synthetic variant considered, the amount of 4b obtained usually is exceptionally low.This is partly ascribed to a consecutive reaction of 4b in acidic methanol affording the chiral diastereomeric bridged biliverdins 5(a and b) and 6(a and b), respectively. - Keywords: Biliverdin-IIIα; Bridged biliverdins; Bilatrienes

ADDITION OF 2-MERCAPTOPROPIONYLGLYCINE TO BILIVERDIN: A KINETIC AND THERMODYNAMIC STUDY

The reaction between biliverdin and 2-mercaptopropionylglycine was studied at 27.5 deg C in DMSO and in aqueous buffer solution (pH 7.4).In the latter medium, the thiol was added to biliverdin either alone or associated with human serum albumin.The equilibrium constants of the reaction carried out in DMSO and in aqueous solution with and without albumin were found to be 40.6E2, 69.2E2, and 1.20E2 M-1, respectively.The kinetics of the reaction carried out in aqueous medium were determined.The results are discussed as a possible model for the photochromic plant photoreceptor phytochrome.

CHIRAL INDUCTION IN BILIVERDIN COVALENTLY BOUND TO AMINO ACIDS

Amidation of the carboxy groups of biliverdin-IXα (2) with the appropiate (S)-amino acid methyl ester yields the optically active derivatives (3)-(8) which exhibit exceedingly strong Cotton effects in their visible and near-u.v. absorption bands.This is due to theinfluence of the chiral centre on the population of helical conformers of the bilatriene moity across five bond lengths.The magnitude of the c.d. observed depends on the steric requirements of the amino acid and the polarity of the solvent.The chiral induction is interpreted in terms of intramolecular interactions of both side chains exerted from different sides of the bilatriene helix by hydrogen bonds.Both the donor and the acceptor sites of the amino acid residues are involved in the chiral association with the bilatriene backbone.