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Université de Neuchâtel

Probing the Active Site of Pseudomonas aeruginosa Porphobilinogen Synthase Using Newly Developed Inhibitors

Frère, Frederic ; Nentwich, Merle ; Gacond, Sabine ; Heinz, Dirk W. ; Neier, Reinhard ; Frankenberg-Dinkel, Nicole

In: Biochemistry, 2006, vol. 45, no. 27, p. 8243–8253

Porphobilinogen synthase catalyzes the first committed step of the tetrapyrrole biosynthesis pathway. In an aldol-like condensation, two molecules of 5-aminolevulinic acid (ALA) form the first pyrrole, porphobilinogen. Newly synthesized analogues of a reaction intermediate of porphobilinogen synthase have been employed in studying the active site and the catalytic mechanism of this early enzyme...

Université de Neuchâtel

Catalytic Hydrogenation of meso-Octamethylporphyrinogen (Calix[4]pyrrole)

Journot, Guillaume ; Letondor, Christophe ; Neier, Reinhard ; Stoeckli-Evans, Helen ; Savoia, Diego ; Gualandi, Andrea

In: Chemistry - A European Journal, 2010, vol. 16, no. 4, p. 4224-4230

Hydrogenation of meso-octamethylporphyrinogen (calix[4]pyrrole) with a number of heterogeneous catalysts under different experimental conditions has been investigated. GC-MS analyses of the reaction mixtures showed the formation of one to four products in low to moderate yields: three of them were diastereoisomers of the product derived from half-hydrogenation of the substrate, and displayed...

Université de Neuchâtel

rac-Methyl 4-azido-3-hydroxy-3-(2-nitrophenyl)butanoate

Vallat, Oliver ; Buciumas, Ana-Maria ; Neier, Reinhard ; Stoeckli-Evans, Helen

In: Acta Crystallographica Section E : Structure Reports Online, 2009, vol. E65, no. 2, p. o396-o397, sup1-8

In the title compound, C11H12N4O5, the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2)°, which avoids steric interactions with the ortho substituents. The hydroxy group is involved in bifurcated hydrogen bonds. The first is an intramolecular O-H···O hydrogen bond, involving the...

Université de Neuchâtel

5-Hydroxyalkyl derivatives of tert-butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate: diastereoselectivity of the Mukaiyama crossed-aldol-type reaction

Vallat, Oliver ; Buciumas, Ana-Maria ; Neier, Reinhard ; Stoeckli-Evans, Helen

In: Acta Crystallographica Section C : Crystal Structure Communications, 2009, vol. C65, no. 4, p. o171-o175

The title compounds, rac-(1'R,2R)-tert-butyl 2-(1'-hydroxyethyl)-3-(2-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate, C17H20N2O6, (I), rac-(1'S,2R)- tert-butyl 2-[1'-hydroxy-3'-(methoxycarbonyl)propyl]-3-(2-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate,...