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Naphthalene-dioxygenase-catalysed cis-dihydroxylation of azaarene derivatives: Part 1: 2-Pyridones and 2-quinolones
Authors:Claude Chopard  Robert Azerad  Thierry Prang
Institution:

aLaboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR 8601 CNRS, Université Paris Descartes, 45 rue des Sts Pères, 75270 Paris cedex 06, France

bLaboratoire de Cristallographie et RMN Biologiques, UMR 8015 CNRS, Université Paris Descartes, 4 avenue de l’Observatoire, 75270 Paris cedex 06, France

Abstract:The scope of the biotransformation of 2-pyridone- and 2-quinolone-derived compounds by recombinant whole-cells of E. coli JM109(DE3)(pDTG141) expressing the naphthalene-dioxygenase system from Pseudomonas sp. NCIB 9816-4 was explored, using a series of N- and C-substituted derivatives. Among them, only the N-methyl substituted compounds were good substrates for a regio- and stereoselective dihydroxylation reaction leading to cis-dihydroxydihydro pyridone derivatives, corresponding to the general pattern expected for this enzyme. In the absence of dihydroxylation reactions, N-dealkylations and monohydroxylations on external methyl groups were observed.
Keywords:N-Methyl-2-pyridone  N-Methyl-2-quinolone  Pseudomonas sp    Dihydroxylation  Naphthalene-dioxygenase
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