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2,4-Bis-(ß-hydroxypropionic Acid) Deuteroporphyrinogen IX, a Possible Intermediate between Coproporphyrinogen III and Protoporphyrin IX

From the ¹ From the Department of Public Health, Faculty of Medicine, Kyoto University, Kyoto, Japan

2,4-Bis-(ß-hydroxypropionic acid) deuteroporphyrin IX tetramethyl ester was synthesized from trans-diacrylic deuteroporphyrin IX and crystallized. The melting point, absorption spectra in the visible region, molar extinction co-efficient, and nuclear magnetic resonance spectra are recorded.

Dehydration of ß-hydroxypropionic acid deuteroporphyrin IX in pyridine with p-toluenesulfonic acid resulted in a mixture of diacrylic acid deuteroporphyrin IX and monohydroxypropionic-monoacrylic deuteroporphyrin IX. No protoporphyrin IX was formed by this method.

Chromic acid-pyridine oxidation of ß-hydroxypropionic acid deuteroporphyrin IX gave a diacetyl deuteroporphyrin IX.

Protoporphyrin IX was obtained in a yield of 45% from an acid-catalyzed reaction of ß-hydroxypropionic acid deuteroporphyrinogen IX.

Diacrylic deuteroporphyrin and monovinyl-monoacrylic deuteroporphyrin IX was obtained from ß-hydroxypropionic acid deuteroporphyrinogen IX at 38° and neutral pH.

Protoporphyrin IX was formed from ß-hydroxypropionic acid deuteroporphyrinogen IX, but not from the oxidized form, in neutral anaerobic incubation with a mitochondrial enzyme.

It is suggested that ß-hydroxypropionic acid deuteroporphyrinogen IX, resulting from an oxygenase-type reaction, is dehydrated and decarboxylated to protoporphyrinogen IX.

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