S. Sano
Nov 25, 1966
Citations
0
Influential Citations
47
Citations
Journal
The Journal of biological chemistry
Abstract
Abstract 2,4-Bis-(β-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 β-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 β-hydroxypropionic acid deuteroporphyrin IX gave a diacetyl deuteroporphyrin IX. Protoporphyrin IX was obtained in a yield of 45% from an acid-catalyzed reaction of β-hydroxypropionic acid deuteroporphyrinogen IX. Diacrylic deuteroporphyrin and monovinyl-monoacrylic deuteroporphyrin IX was obtained from β-hydroxypropionic acid deuteroporphyrinogen IX at 38° and neutral pH. Protoporphyrin IX was formed from β-hydroxypropionic acid deuteroporphyrinogen IX, but not from the oxidized form, in neutral anaerobic incubation with a mitochondrial enzyme. It is suggested that β-hydroxypropionic acid deuteroporphyrinogen IX, resulting from an oxygenase-type reaction, is dehydrated and decarboxylated to protoporphyrinogen IX.