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Issue 21, 1996
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Synthesis of analogues of porphobilinogen


Syntheses are described of several analogues of porphobilinogen intended as substrates and/or inhibitors of porphobilinogen deaminase (hydroxymethylbilane synthase). 2-Methylporphobilinogen 12 has been synthesised from α-methylpyrrole 6, whereas a phosphonate analogue 20 of porphobilinogen, 8,9-didehydroporphobilinogen 26 and 9-fluoroporphobilinogen 38 have all been made from the 1H-pyrrolo[2,3-c]pyridine 14. The best route to 38 avoids fluoroacrylate 28 because of loss of fluorine during reduction of the double bond.

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Article type: Paper
DOI: 10.1039/P19960002633
Citation: J. Chem. Soc., Perkin Trans. 1, 1996,0, 2633-2642
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    Synthesis of analogues of porphobilinogen

    F. J. Leeper, M. Rock and D. Appleton, J. Chem. Soc., Perkin Trans. 1, 1996, 0, 2633
    DOI: 10.1039/P19960002633

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