scholarly journals The isolation and further characterization of the bilirubin tetrapyrroles in bile-containing human duodenal juice and dog gall-bladder bile

1977 ◽  
Vol 167 (1) ◽  
pp. 1-8 ◽  
Author(s):  
Ellen R. Gordon ◽  
Tak-Hang Chan ◽  
Karen Samodai ◽  
Carl A. Goresky
Keyword(s):  
Mass Spectrometry ◽  
Gall Bladder ◽  
Total Bilirubin ◽  
Molar Ratio ◽  
Diazonium Salts ◽  
Duodenal Juice ◽  
Human Bile ◽  
Total Pigment ◽  
The Individual

Bilirubin and its conjugates were extracted from either dog gall-bladder bile or bile-containing human duodenal juice into chloroform containing 10mm-tetraheptylammonium chloride. The intact bilirubin tetrapyrroles were then separated by t.l.c. Structural elucidation was made after coupling of the individual pigments with diazonium salts. Four azopigments were detected: azopigment αo or dipyrrolic azobilirubin; azopigment δ or dipyrrolic azobilirubin monoglucuronide; azopigment α3 or dipyrrolic azobilirubin monoglucoside; and, from dog gall-bladder bile, azopigment α2. The last conjugate required further verification of its structure. After methanolysis, it was shown by combined g.l.c.–mass spectrometry to contain xylose in a 1:1 molar ratio with the azopigments of bilirubin. Human bile contained 86% bilirubin diglucuronide, 7% bilirubin monoglucuronide monoglucoside diester, 4% bilirubin monoglucuronide and 3% bilirubin. Dog gall-bladder bile had a considerably different composition; it contained 47% bilirubin diglucuronide, 40% bilirubin monoglucuronide monoglucoside diester, 8% bilirubin monoglucuronide, 4% bilirubin diglucoside, 1–2% bilirubin and traces of conjugates containing xylose. The total bilirubin content and proportions of the conjugates did not change in bile that was frozen and stored at −20°C under N2, whereas in the chloroform/tetraheptylammonium chloride extract, similarly stored, total pigment was slowly lost and the diglucuronide conjugate converted into the monoglucuronide.

scholarly journals The isolation and characterization of bilirubin diglucuronide, the major bilirubin conjugate in dog and human bile

1976 ◽  
Vol 155 (3) ◽  
pp. 477-486 ◽  
Author(s):  
E R Gordon ◽  
C A Goresky ◽  
T H Chang ◽  
A S Perlin
Keyword(s):  
Mass Spectrometry ◽  
Glucuronic Acid ◽  
Methyl Esters ◽  
Water Soluble ◽  
Molar Ratio ◽  
Human Bile ◽  
Isolation And Characterization ◽  
Azo Derivatives ◽  
Derivatives Of

The chemical structure of the major conjugate of bilirubin was unequivocally elucidated by structural analysis. The conjugated bilirubins were first separated from the lipid components of human duodenal aspirates or dog gall-bladder bile, and then resolved by t.l.c. into a series of tetrapyrroles. The major tetrapyrrole was then converted into its more stable dipyrrolic azo derivative for further analysis. The conjugated moiety of the azopigment was characterized after methanolysis with sodium methoxide. This reaction yields two types of product, those soluble in water and those soluble in organic solvents. The organic-soluble fraction was shown by t.l.c. and mass spectrometry to contain the methyl esters of the dipyrrolic azo derivatives of bilirubin. The water-soluble materials were analysed by enzymic procedures, t.l.c., n.m.r. spectrometry and combined g.l.c. and mass spectrometry. This analysis showed that the only water-soluble product resulting from the methanolysis was glucuronic acid. The structure was identical with that of pure standards, on both mass spectrometry and n.m.r. spectroscopy. No contaminating moieties were found. Quantitative measurement indicated that the glucuronic acid had been released in a 1:1 molar ratio with the resulting methyl esters of the dipyrrolic azo derivatives of bilirubin. This unequivocally establishes bilirubin diglucuronide as the major pigment present in bile. Past problems with identification of bilirubin diglucuronide were shown to originate from procedures which resulted in incomplete separation and isolation of the azopigments of the conjugated bilirubins, owing to contamination by biliary lipids.

Isolation and Characterization of the Photoalteration Products of cis- and trans-Chlordane

1975 ◽  
Vol 58 (1) ◽  
pp. 6-9
Author(s):  
Francis I Onuska ◽  
Michael E Comba
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Thin Layer ◽  
High Yield ◽  
Isolation And Characterization ◽  
The Individual ◽  
Cis And Trans ◽  
Layer Chromatography

Abstract Ultraviolet irradiation of cis- and trares-chlordane yielded 3 photolysis products. The expected half-caged analog of cis-chlordane was formed in high yield, and 2 minor photoproducts of trans-chlordane were observed. One of these products was a half-caged isomer. The individual photoproducts were isolated by thin layer chromatography and characterized by infrared, nuclear magnetic resonance, and mass spectrometry.

Triazene derivatives of (1,x)-diazacycloalkanes. Part III. Synthesis and characterization of a series of 1,4-di[2-aryl-1-diazenyl]piperazines

2005 ◽  
Vol 83 (5) ◽  
pp. 471-476 ◽  
Author(s):  
Vanessa Renée Little ◽  
Reid Tingley ◽  
Keith Vaughan
Keyword(s):  
Mass Measurement ◽  
Variable Temperature ◽  
Molar Ratio ◽  
Diazonium Salts ◽  
Piperazine Ring ◽  
Nmr Data ◽  
Ir And Nmr Spectroscopy ◽  
Reported Data ◽  
Derivatives Of

Reaction of a series of diazonium salts with piperazine in a 2:1 molar ratio affords excellent yields of the 1,4-di-[2-aryl-1-diazenyl]piperazines (3), which have been characterized by IR and NMR spectroscopy. Structural characterization is supported by elemental analysis or by mass spectrometry with accurate mass measurement of the molecular ion. The protons of the piperazine ring hydrogens give rise to a sharp singlet at ca. 4 ppm in the NMR spectra, indicating that the conformational equilibrium in the piperazine ring is rapid on the NMR timescale. The four equivalent carbon atoms of the piperazine ring resonate in the range 46–48 ppm. A variable temperature NMR experiment suggests that there is restricted rotation around the N2—N3 bond of the triazene moiety in 3. The NMR data compares favorably with previous reported data for 1-aryldiazenyl-4-methylpiperazines (1) and 1,4-di-(2-aryldiazen-1-yl)homopiperazines (2b).Key words: triazene, piperazine, diazonium coupling, NMR.

scholarly journals Synthesis and spectral characterization of stannocanes of the type [O(CH2CH2S)2SnR2](R=Me1,Bun2,Ph3)

2013 ◽  
Vol 11 (7) ◽  
pp. 1248-1254
Author(s):  
Abbas Tarassoli ◽  
Adibeh Kord
Keyword(s):  
Mass Spectrometry ◽  
Sodium Ethoxide ◽  
Inert Atmosphere ◽  
Molar Ratio ◽  
Improved Method ◽  
119Sn Nmr ◽  
Ft Ir ◽  
Organotin Species ◽  
Secondary Bonding

AbstractThe stannocanes of the type [O(CH2CH2S)2SnR2](R=Me1,Bun2,Ph3) have been synthesized in an improved method by the reaction of R2SnCl2 with 2, 2′-oxydiethanethiol O(CH2CH2SH)2 in molar ratio of 1:1 at the presence of sodium ethoxide in anhydrous ethanol. The reactions are carried out under inert atmosphere. These compounds have been extensively characterized by FT-IR, UV-Vis spectrophotometry, multi-nuclear (1H, 13C, 119Sn) NMR, elemental analysis and mass spectrometry. The obtained data clearly indicates that, there is a strong interaction between oxygen atom of the ligand as a donor and Sn atom of the organotin species as a Lewis acid acceptor. Therefore, the resulted dithiostannocanes possess a transannular secondary bonding and hypervalency at the central Sn atom which leads to an increase in the coordination number of tin from four to five-coordinated tin.

Deep proteomic characterization of fiber types of murine muscles by laser microdissection and mass spectrometry

2019 ◽  
Author(s):  
B Eggers ◽  
K Schork ◽  
R Schröder ◽  
CS Clemen ◽  
C Berwanger ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Laser Microdissection ◽  
Fiber Types
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