The chemistry of heteroarylphosphorus compounds. Part II. The importance of inductive effects on pre-equilibria in the alkaline hydrolysis of heteroarylphosphonium salts; phosphorus-31 nuclear magnetic resonance studies

1972 ◽  
pp. 63 ◽  
Author(s):  
David W. Allen ◽  
B. G. Hutley ◽  
Malcolm T. J. Mellor
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Alkaline Hydrolysis ◽  
Magnetic Resonance Studies ◽  
Inductive Effects ◽  
Hydrolysis Of ◽  
Nuclear Magnetic

scholarly journals The isolation of an azobilirubin β-d-monoglucoside from dog gall-bladder bile

1974 ◽  
Vol 143 (1) ◽  
pp. 97-105 ◽  
Author(s):  
Ellen R. Gordon ◽  
Molly Dadoun ◽  
Carl A. Goresky ◽  
Tak-Hang Chan ◽  
Arthur S. Perlin
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Gall Bladder ◽  
Alkaline Hydrolysis ◽  
Sodium Methoxide ◽  
Water Soluble ◽  
Hydrolysis Of ◽  
Conjugated Bilirubin ◽  
Nuclear Magnetic

An ethyl anthranilate azopigment of bilirubin conjugated to β-d-monoglucoside was isolated from dog gall-bladder bile. Glucose was cleaved from the azopigment by treatment with β-glucosidase and β-glucuronidase. Mild alkaline hydrolysis of the compound by sodium methoxide yielded two kinds of compounds, water-soluble and organic-soluble. The former were shown, by enzymic analysis, t.l.c., nuclear magnetic resonance, and combined g.l.c. and mass spectrometry, to contain glucose. No evidence was obtained from these data that a disaccharide was present in this fraction. The organic-soluble compounds formed during this methanolysis were shown, by t.l.c. and mass spectrometry, to be the isomeric dipyrrole azopigments of bilirubin. These findings contribute further evidence to the controversy surrounding the nature of conjugated bilirubin.

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