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Biosynthesis of porphyrins and related macro cycles part 6 nature of the rearrangement process leading to the natural type iii porphyrins



Biosynthesis of porphyrins and related macro cycles part 6 nature of the rearrangement process leading to the natural type iii porphyrins



Journal of the Chemical Society Perkin Transactions I (3): 273-282



Logical analysis of the problem posed by the constant formation in nature of type III porphyrins, e.g., protoporphyrin-IX, focuses attention on C.sbd.C bond making and bond breaking around the carbon atoms from which the interpyrrolic bridges are built (at C-5, C-10, C-15 and C-20). An approach to the study of such processes is outlined, based on double [13C] labeling combined with NMR spectroscopy. [2,11-13C2]Porphobilinogen was prepared and applied to determine the size of 13C.sbd.13C coupling for directly bonded carbon atoms in the porphyrin macrocycle and to indicate that a biosynthetically significant 13C.sbd.13C coupling occurs between carbon atoms separated by 3 bonds. A coupled enzyme system was developed from chicken blood cells and beef liver mitochondria which produces sufficient protoporphyrin-IX for spectroscopic and chemical work (20-30 mg); a similar system from Euglena gracilis is also described. [2,11-13C2]Porphobilinogen diluted with unlabeled porphobilinogen was converted enzymically into protoporphyrin-IX; the 13C spectra of the dimethyl ester as such, with a praseodymium shift reagent and after chemical modification establish that the formation of type III porphyrins by both enzyme systems (avian and algal) is characterized by the same 3 precise features which are described.

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Accession: 004843447

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PMID: 942966


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