140870-34-4Relevant academic research and scientific papers
Synthesis of analogues of porphobilinogen
Leeper, Finian J.,Rock, Martin,Appleton, Diana
, p. 2633 - 2642 (2007/10/03)
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.
Modified Substrates for Tetrapyrrole Biosynthesis: Analogues of Porphobilinogen Showing Unusual Inhibition of Porphobilinogen Deaminase
Leeper, Finian J.,Rock, Martin
, p. 242 - 244 (2007/10/02)
Syntheses are described of two analogues of porphobilinogen (PBG), a fluoro derivative 10 and a phosphonate 13, which are the first known unnatural substrates of PBG deaminase; when they act as inhibitors of the reaction of PBG, these compounds produce unusual sigmoidal kinetics, explained by their involvement as poor substrates in the particular mechanism of this enzyme.
