Anaerobic and Aerobic Coproporphyrinogen III Oxidases of Rhodopseudomonas Spheroides. Mechanism and Stereochemistry of Vinyl Group Formation

Overview

Journal Biochem J

Specialty Biochemistry

Date 1983 Mar 1

PMID 6603215

Citations 18

Authors

J S Seehra

P M Jordan

M Akhtar

Affiliations

Soon will be listed here.

Abstract

An improved method for the preparation of various species of porphobilinogen stereospecifically labelled with 3H in the side chains (at C-6, C-7 and C-8) is described. These labelled samples were used to study the mechanism and stereochemistry of anaerobic as well as aerobic coproporphyrinogen III oxidase of light-grown Rhodopseudomonas spheroides. It was shown that both the oxidases catalyse the conversion of the propionate side chains of coproporphyrinogen III into the vinyl groups of protoporphyrinogen IX, (formula; see text) with the labilization of the pro-S-hydrogen atom at the beta-position. These results are similar to those previously recorded for such conversions in animal and plant systems. In the light of the cumulative information available to date, mechanisms for the conversion, (formula; see text) are discussed and doubt is cast on the participation of hydroxylated intermediates in the process.

Citing Articles

Trapping the substrate radical of heme synthase AhbD.

Heidinger L, Fix I, Friedrich T, Layer G Front Chem. 2024; 12:1430796.

PMID: 39119521 PMC: 11306076. DOI: 10.3389/fchem.2024.1430796.

Radical SAM Enzymes Involved in Tetrapyrrole Biosynthesis and Insertion.

Layer G, Jahn M, Moser J, Jahn D ACS Bio Med Chem Au. 2023; 2(3):196-204.

PMID: 37101575 PMC: 10114771. DOI: 10.1021/acsbiomedchemau.1c00061.

Making and breaking carbon-carbon bonds in class C radical SAM methyltransferases.

Brimberry M, Mathew L, Lanzilotta W J Inorg Biochem. 2021; 226:111636.

PMID: 34717253 PMC: 8667262. DOI: 10.1016/j.jinorgbio.2021.111636.

Prokaryotic Heme Biosynthesis: Multiple Pathways to a Common Essential Product.

Dailey H, Dailey T, Gerdes S, Jahn D, Jahn M, OBrian M Microbiol Mol Biol Rev. 2017; 81(1).

PMID: 28123057 PMC: 5312243. DOI: 10.1128/MMBR.00048-16.

Heme Synthesis and Acquisition in Bacterial Pathogens.

Choby J, Skaar E J Mol Biol. 2016; 428(17):3408-28.

PMID: 27019298 PMC: 5125930. DOI: 10.1016/j.jmb.2016.03.018.

References

Ehteshamuddin A . Anaerobic formation of protoporphyrin IX from coproporphyrinogen III by bacterial preparations. Biochem J. 1968; 107(3):446-7. PMC: 1198683. DOI: 10.1042/bj1070446. View

TAIT G . Coproporphyrinogenase activities in extracts of Rhodopseudomonas spheroides and Chromatium strain D. Biochem J. 1972; 128(5):1159-69. PMC: 1174004. DOI: 10.1042/bj1281159. View

Zaman Z, Jordan P, Akhtar M . Mechanism and stereochemistry of the 5-aminolaevulinate synthetase reaction. Biochem J. 1973; 135(2):257-63. PMC: 1165818. DOI: 10.1042/bj1350257. View

Cavaleiro J, KENNER G, Smith K . Pyrroles and related compounds. XXXII. Biosynthesis of protoporphyrin-IX from coproporphyrinogen-3. J Chem Soc Perkin 1. 1974; 10(0):1188-94. DOI: 10.1039/p19740001188. View

Zaman Z, Akhtar M . Mechanism and stereochemistry of vinyl-group formation in haem biosynthesis. Eur J Biochem. 1976; 61(1):215-23. DOI: 10.1111/j.1432-1033.1976.tb10014.x. View

BATTERSBY A . The discovery of nature's biosynthetic pathways. Experientia. 1978; 34(1):1-13. DOI: 10.1007/BF01921870. View

Yoshinaga T, Sano S . Coproporphyrinogen oxidase. II. Reaction mechanism and role of tyrosine residues on the activity. J Biol Chem. 1980; 255(10):4727-31. View

Barnard G, Akhtar M . Stereochemical and mechanistic studies on the decarboxylation of uroporphyrinogen III in haem biosynthesis. J Chem Soc Perkin 1. 1979; 10:2354-60. DOI: 10.1039/p19790002354. View

Mauzerall D, Granick S . The occurrence and determination of delta-amino-levulinic acid and porphobilinogen in urine. J Biol Chem. 1956; 219(1):435-46. View

10.

Ellman G . Tissue sulfhydryl groups. Arch Biochem Biophys. 1959; 82(1):70-7. DOI: 10.1016/0003-9861(59)90090-6. View

11.

Rose Z . Studies on the mechanism of action of isocitric dehydrogenase. J Biol Chem. 1960; 235:928-33. View

12.

Lienhard G, Rose I . THE STEREOCHEMISTRY OF DECARBOXYLATION OF ISOCITRATE BY ISOCITRIC ACID DEHYDROGENASE. Biochemistry. 1964; 3:185-90. DOI: 10.1021/bi00890a008. View

13.

LASCELLES J . The synthesis of porphyrins and bacteriochlorophyll by cell suspensions of Rhodopseudomonas spheroides. Biochem J. 1956; 62(1):78-93. PMC: 1274515. DOI: 10.1042/bj0620078. View