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Issue 23, 1993
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Biosynthesis of porphyrins and related macrocycles. Part 41. Fate of oxygen atoms as precorrin-2 carrying eight labelled carboxyl groups (13C18O2H) is enzymatically converted into cobyrinic acid

Abstract

5-Amino[1,4-13C2]laevulinic acid and 5-amino[1-13C]laevulinic acid are synthesised and all three 16O atoms of the latter are exchanged for 18O. The 13C,18O-labelled material is then converted in vitro into precorrin-2 2 by the combined action of four genetically overproduced enzymes. The product is isolated in its aromatised form, sirohydrochlorin 10 and 13C-NMR shows that all 8 carboxyl groups of 10 retain both oxygen atoms throughout the biosynthesis. A cell-free enzyme preparation from Propionibacterium shermanii converts the 13C,18O-labelled sirohydrochlorin 10via2 into cobyrinic acid 4, a late precursor of vitamin B12. 13C-NMR proves that 6 carboxyl groups of cobyrinic acid (b–g, inclusive) retain both oxygen atoms whereas the a-carboxyl group undergoes specific loss of one labelled oxygen atom.

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Article type: Paper
DOI: 10.1039/P19930002893
Citation: J. Chem. Soc., Perkin Trans. 1, 1993,0, 2893-2899
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    Biosynthesis of porphyrins and related macrocycles. Part 41. Fate of oxygen atoms as precorrin-2 carrying eight labelled carboxyl groups (13C18O2H) is enzymatically converted into cobyrinic acid

    R. A. Vishwakarma, S. Balachandran, A. I. D. Alanine, N. P. J. Stamford, F. Kiuchi, F. J. Leeper and A. R. Battersby, J. Chem. Soc., Perkin Trans. 1, 1993, 0, 2893
    DOI: 10.1039/P19930002893

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