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Issue 8, 1999
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Biosynthesis of porphyrins and related macrocycles. Part 51.1,2 Proof that a reductive step occurs during the biosynthesis of vitamin B12 by the microaerophilic organism, Propionibacterium shermanii

Abstract

5-Amino[4-13C]laevulinic acid has been synthesised for enzymic conversion into 13C-labelled precorrin-2 12a. This was incubated with an enzyme system from Propionibacterium shermanii in the presence of [4-2H2]NADH 5a and [4-2H2]NADPH 6a to yield cobyrinic acid 15a, shown to carry 2H at C-19 by appropriate 13C-NMR studies. The same reducing cofactors but now stereospecifically labelled at C-4 with tritium were similarly used to biosynthesise cobyrinic acid which was 3H-labelled (15b) from the 4(R)-cofactors but carried no 3H (15c) when the 4(S )-cofactors were used. Suitable degradation of the cobyrinic acid 15b after conversion into its ester 16b proved 3H-labelling at C-19. These results establish that the biosynthesis of vitamin B12 in the microaerophilic organism Pr. shermanii involves a reductive step in which a reductase enzyme transfers 4-HR of the cofactor to C-19 of the macrocycle.

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Article type: Paper
DOI: 10.1039/A809858A
Citation: J. Chem. Soc., Perkin Trans. 1, 1999,0, 879-888
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    Biosynthesis of porphyrins and related macrocycles. Part 51.1,2 Proof that a reductive step occurs during the biosynthesis of vitamin B12 by the microaerophilic organism, Propionibacterium shermanii

    K. Ichinose, M. Kodera, F. J. Leeper and A. R. Battersby, J. Chem. Soc., Perkin Trans. 1, 1999, 0, 879
    DOI: 10.1039/A809858A

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