scholarly journals The 3H-labelling of bilirubin

1976 ◽  
Vol 157 (2) ◽  
pp. 511-512 ◽  
Author(s):  
F E Hancock ◽  
D W Hutchinson ◽  
A J Knell
Keyword(s):  
Propionic Acid ◽  
Dimethyl Ester ◽  
Side Chains ◽  
Simple Method

A simple method has been developed for the preparation of 3H-labelled bilirubin IX-alpha from bilirubin dimethyl ester. The label is located in the propionic acid side chains, and there is no isomerization of the bilirubin during the preparation.

scholarly journals Microbiological degradation of bile acids. The preparation of hexahydroindane derivatives as substrates for studying cholic acid degradation

1977 ◽  
Vol 164 (3) ◽  
pp. 709-714 ◽  
Author(s):  
S Hayakawa ◽  
T Takata ◽  
T Fujiwara ◽  
S Hashimoto
Keyword(s):  
Carboxylic Acid ◽  
Cholic Acid ◽  
Propionic Acid ◽  
Good Yield ◽  
Degradation Products ◽  
Chemical Oxidation ◽  
Compound Iiib ◽  
Partial Synthesis ◽  
Arthrobacter Simplex ◽  
Simple Method

Relatively large amounts of 3-(3aalpha-hexahydro-7abeta-methyl-1,5-dioxoindan-4alpha-yl)propionic acid (IIb), which is believed to be one of the intermediates involved in the degradation of cholic acid (I), were needed to identify is further degradation products. A simple method for the preparation of this compound was then investigated. Arthrobacter simplex could degrade-3-oxoandrost-4-ene-17beta-carboxylic acid (IIIa) to 3-(1beta-carboxy-3aalpha-hexahydro-7abeta-methyl-5-oxoindan-4alpha-yl)propionic acid (IVa) in good yield, the structure of which was established by partial synthesis. It was therefore expected that, if a similar degradation by this organism occurred with 17alpha-hydroxy-3-oxoandrost-4-ene-17beta-carboxylic acid (IIIb), which is easily obtained by chemical oxidation of commercially availabe 17alpha-hydroxydeoxycorticosterone, the resulting product, 3-(1beta-carboxy-3aalpha-hexahydro-1alpha-hydroxy-7abeta-methyl-5-oxoindan-4alpha-yl)propionic acid (IVb), could be readily converted chemically into the required dioxocarboxylic acid, (IIb). Exposure of compound (IIIb) to A. simplex produced, as expected, compound (IVb) which was then oxidized with NaBiO3 to give a reasonable yield of compound (IIb).

Exploring the Conformational Variability in the Heme b Propionic Acid Side Chains through the Effect of a Biological Probe: A Study of the Isolated Ions

2015 ◽  
Vol 119 (5) ◽  
pp. 1919-1929 ◽  
Author(s):  
Alberto De Petris ◽  
Barbara Chiavarino ◽  
Maria Elisa Crestoni ◽  
Cecilia Coletti ◽  
Nazzareno Re ◽  
...  
Keyword(s):  
Propionic Acid ◽  
Side Chains ◽  
Conformational Variability ◽  
Biological Probe

Synthesis and conformation of a bilirubin analog with propionic acid side chains extended to undecanoic acid

Tetrahedron ◽  
1992 ◽  
Vol 48 (29) ◽  
pp. 5969-5984 ◽  
Author(s):  
John Chiefari ◽  
Richard V. Person ◽  
David A. Lightner
Keyword(s):  
Propionic Acid ◽  
Side Chains ◽  
Undecanoic Acid

Synthesis of 3-(p-Carboxyphenoxy) propionic Acid and Its Dimethyl Ester

1972 ◽  
pp. 1534-1535 ◽  
Author(s):  
Taketoshi KITO ◽  
Kimio SHIMOYAMA ◽  
Ichiro HIRAO
Keyword(s):  
Propionic Acid ◽  
Dimethyl Ester

The preparation of porphyrin S-411 (dehydrocoproporphyrin) and harderoporphyrin from protoporphyrin IX

1981 ◽  
Vol 59 (5) ◽  
pp. 779-785 ◽  
Author(s):  
David Dolphin ◽  
Ramani Sivasothy
Keyword(s):  
Dimethyl Ester ◽  
Protoporphyrin Ix ◽  
The Other ◽  
Side Chain ◽  
Side Chains ◽  
Positional Isomers ◽  
Other Hand ◽  
Hydroxyethyl Group

Protoporphyrin IX dimethyl ester has been converted into the two 2,4-positional isomers bearing hydroxyethyl and methoxycarbonylvinyl side chains. The 4-(2-hydroxyethyl) group was extended to a methoxycarbonylethyl group to give the tetramethyl ester of porphyrin S-411 (2-methoxycarbonylvinyl-4-methoxycarbonylethyldeuteroporphyrin dimethyl ester). On the other hand reduction of the 4-methoxycarbonylvinyl to the corresponding methoxycarbonylethyl group and dehydration of the 2-(2-hydroxyethyl) to a vinyl side chain gave the trimethyl ester of harderoporphyrin (2-vinyl-4-methoxycarbonylethyldeuteroporphyrin dimethyl ester).

scholarly journals THE PORPHYRIN REQUIREMENTS OF HAEMOPHILUS INFLUENZAE AND SOME FUNCTIONS OF THE VINYL AND PROPIONIC ACID SIDE CHAINS OF HEME

1946 ◽  
Vol 30 (1) ◽  
pp. 1-13 ◽  
Author(s):  
S. Granick ◽  
H. Gilder
Keyword(s):  
Propionic Acid ◽  
Protoporphyrin Ix ◽  
Anomalous Behavior ◽  
Side Chains ◽  
Iron Porphyrins ◽  
Heme Enzymes ◽  
Low Concentrations ◽  
Rough Strain ◽  
Growth Promoting ◽  
Iron Protoporphyrin

1. Iron protoporphyrin IX was required for the growth of H. influenzae. It could be replaced by protoporphyrin IX. When grown on protoporphyrin evidence was obtained for the presence of Fe porphyrin in the organism. It was concluded that the organism could insert iron into the protoporphyrin ring. 2. In the smooth strains, other porphyrins containing no iron such as deutero-, hemato-, meso-, and coproporphyrins could not replace protoporphyrin for growth. Since protoporphyrin has two vinyl groups which other porphyrins lack, it was concluded that the two vinyl groups were essential for growth. 3. When porphyrins lacking vinyl groups were converted chemically into iron porphyrins and then supplied to the organisms it was found that these iron porphyrins supported growth. It was concluded that the "smooth" organisms were able to insert iron only into the porphyrin containing the vinyl groups; i.e., protoporphyrin. One function of the vinyl groups then was to permit iron to be inserted biologically into the porphyrin ring. 4. An anomalous behavior in the rough Turner strain was observed and discussed. This organism was able to insert iron into mesoporphyrin at low concentrations but was inhibited by this compound at higher concentrations. In all other reactions with the porphyrins this rough strain behaved in the same was as did the smooth strains. 5. All strains which were grown on iron porphyrins lacking vinyl groups could not reduce nitrate to nitrite. When grown on protoporphyrin or Fe protoporphyrin reduction of nitrate occurred. It was concluded that the nitrate-reducing mechanism required the presence of the vinyl groups either for its formation or function. 6. The porphyrins lacking iron and lacking vinyl groups inhibited the growth of H. influenzae on Fe protoporphyrin. The inhibition between a porphyrin and Fe protoporphyrin was a competitive one. It was suggested that the porphyrin inhibited the growth-promoting properties of Fe protoporphyrin by attaching on to a particular apoprotein, thus preventing the formation of a heme catalyst. Likewise, competition between two growth-promoting Fe porphyrins for apoenzymes could be shown to occur. 7. Protoporphyrin and Fe protoporphyrin supported growth. When their propionic acid side chains were esterified they no longer supported growth. It was suggested that the esterified carboxyl groups could not attach to the specific apoproteins to form the heme enzymes and so could not act to support growth. For the same reason the inhibitory action of porphyrins lacking vinyl groups could be prevented by esterifying their propionic acid groups.

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