48134-75-4Relevant academic research and scientific papers
The kinetic analysis of the N-methylation of 4-phenylpyridine by nicotinamide N-methyltransferase: Evidence for a novel mechanism of substrate inhibition
van Haren, Matthijs J.,Thomas, Martin G.,Sartini, Davide,Barlow, David J.,Ramsden, David B.,Emanuelli, Monica,Klamt, Fábio,Martin, Nathaniel I.,Parsons, Richard B.
, p. 127 - 136 (2018)
The N-methylation of 4-phenylpyridine produces the neurotoxin 1-methyl-4-phenylpyridinium ion (MPP+). We investigated the kinetics of 4-phenylpyridine N-methylation by nicotinamide N-methyltransferase (NNMT) and its effect upon 4-phenylpyridine toxicity i
Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines
Toscani, Anita,Risi, Caterina,Black, Gary W.,Brown, Nicola L.,Shaaban, Ali,Turner, Nicholas J.,Castagnolo, Daniele
, p. 8781 - 8787 (2018/09/06)
A sustainable MAO-N biocatalyzed process for the synthesis of pyridines from aliphatic tetrahydropyridines (THP) has been developed. Pyridine compounds were synthesized under mild reaction conditions and with high conversion, exploiting MAO-N whole cells as aromatizing biocatalysts. The kinetic profile of the whole cell biocatalytic transformation was finally investigated via in situ 19F NMR.
Chemical model studies on the monoamine oxidase-B catalyzed oxidation of 4-substituted 1-cyclopropyl-1,2,3,6-tetrahydropyridines
Franot, Christelle,Mabic, Stephane,Castagnol Jr., Neal
, p. 283 - 291 (2007/10/03)
Two catalytic pathways have been proposed for the flavoenzyme monoamine oxidase B (MAO-B-one based on an initial single electron transfer (SET) step from the nitrogen lone pair and the second based on an initial α-carbon hydrogen atom transfer (HAT) step. The SET pathway is consistent with the mechanism based inactivation properties of various cyclopropylamines. The observation that MAO-B catalyzes the efficient oxidation of certain 1- cyclopropyl-4-substituted-1,2,3,6-tetrahydropyridines to the corresponding dihydropyridinium metabolites suggests that the catalytic pathway for these cyclic tertiary allylamines may not proceed via the putative SET generated aminyl radical cations. The present paper describes the chemical fate of a series of N-cyclopropyltetrahydropyridines examined under reaction conditions that model the SET and the HAT pathways. All of the test compounds were rapidly converted under HAT reaction conditions to their dihydropyridinium products. Although the test compounds also were oxidized rapidly under SET conditions, no evidence for dihydropyridinium product formation was observed. The products that were identified most likely were formed after cyclopropyl ring opening of the initially formed cyclopropylaminyl radical cation. The results are discussed in terms of the mechanism of MAO-B catalysis.
