title: Biocatalysed halogenation of nucleobase analogues.
abstract: The synthesis of halogenated nucleosides and nucleobases is of interest due to their chemical and pharmacological applications. Herein, the enzymatic halogenation of nucleobases and analogues catalysed by microorganisms and by chloroperoxidase from Caldariomyces fumago has been studied. This latter enzyme catalysed the chlorination and bromination of indoline and uracil. Pseudomonas, Citrobacter, Aeromonas, Streptomyces, Xanthomonas, and Bacillus genera catalysed the chlorination and/or bromination of indole and indoline. Different products were obtained depending on the substrate, the biocatalyst and the halide used. In particular, 85% conversion from indole to 5-bromoindole was achieved using Streptomyces cetonii.
authors.affiliation: Biotransformation Laboratory, Universidad Nacional de Quilmes, R. S. Peña 352 Bernal, 1876 Buenos Aires, Argentina.
authors.forename: Rosario
authors.initials: R
authors.lastname: Médici
authors.forename: Juan Ignacio
authors.initials: JI
authors.lastname: Garaycoechea
authors.forename: Lucas Andrés
authors.initials: LA
authors.lastname: Dettorre
authors.forename: Adolfo Marcelo
authors.initials: AM
authors.lastname: Iribarren
authors.forename: Elizabeth Sandra
authors.initials: ES
authors.lastname: Lewkowicz
mesh_terms: D001203:Ascomycota / Q000201:enzymology / Q000378:metabolism*; D001419:Bacteria / Q000378:metabolism; D055162:Biocatalysis; D002711:Chloride Peroxidase / Q000378:metabolism*; D003512:Cyclohexanones / Q000378:metabolism; D054879:Halogenation; D006846:Hydrocarbons, Halogenated / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism*; D014498:Uracil / Q000031:analogs & derivatives* / Q000378:metabolism
chemical_list: D003512:Cyclohexanones; D006846:Hydrocarbons, Halogenated; D007211:Indoles; D014498:Uracil; C057812:indoline; C006991:chlorodimedone; D002711:Chloride Peroxidase