Non-enzymatic heme formation in the presence of fatty acids and thiol reductants.
Non-enzymatic heme formation from equimolar amounts of porphyrin and iron was investigated. When mesoporphyrin IX and iron citrate were incubated with oleic acid and dithiothreitol at 37 degrees C in vacuo, mesoheme was formed in a high yield. When protoporphyrin IX and deuteroporphyrin IX were used, protoheme and deuteroheme were formed, respectively. Cysteine or 2-mercaptoethanol instead of dithiothreitol also resulted in the formation of heme. Linoleic acid was as effective as oleic acid, but at 37 degrees C, saturated fatty acids and phospholipids gave low yields. When incubation was at 70 degrees C saturated fatty acids as well as unsaturated fatty acids produced a large amount of heme. The optimum pH was 8.8. By increasing the concentration of Triton X-100 to 0.1%, heme formation decreased, and at concentrations above this level, completely disappeared. The conditions of non-enzymatic heme reaction presented here seem to be useful in elucidation of the mechanism of metalloporphyrin formation.
D005227:Fatty Acids; D006418:Heme / Q000138:chemical synthesis*; D007700:Kinetics; D010084:Oxidation-Reduction; D010743:Phospholipids; D011166:Porphyrins; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds
D005227:Fatty Acids; D010743:Phospholipids; D011166:Porphyrins; D013438:Sulfhydryl Compounds; D006418:Heme