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Issue 17, 1996
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Biosynthesis of porphyrins and related macrocycles. Part 44. Synthetic and stereochemical studies on the proposed spiro intermediate for biosynthesis of the natural porphyrins

Abstract

A route is devised for synthesis of both enantiomers of the spiro lactam 4. The enzyme uroporphyrinogen III synthase (cosynthetase), which converts hydroxymethylbilane 1 into uroporphyrinogen III 3, is competitively inhibited more than twenty times more strongly by one enantiomer of 4 than by the other. This finding adds further strong support to the view that cosynthetase acts by generating the spiro pyrrolenine 2 as an intermediate.

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Article type: Paper
DOI: 10.1039/P19960002079
Citation: J. Chem. Soc., Perkin Trans. 1, 1996,0, 2079-2090
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    Biosynthesis of porphyrins and related macrocycles. Part 44. Synthetic and stereochemical studies on the proposed spiro intermediate for biosynthesis of the natural porphyrins

    M. A. Cassidy, N. Crockett, F. J. Leeper and A. R. Battersby, J. Chem. Soc., Perkin Trans. 1, 1996, 0, 2079
    DOI: 10.1039/P19960002079

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