Biocatalysed halogenation of nucleobase analogues
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...
| Autores principales: | , , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_01415492_v33_n10_p1999_Medici |
| Aporte de: |
| id |
todo:paper_01415492_v33_n10_p1999_Medici |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_01415492_v33_n10_p1999_Medici2023-10-03T14:58:41Z Biocatalysed halogenation of nucleobase analogues Médici, R. Garaycoechea, J.I. Dettorre, L.A. Iribarren, A.M. Lewkowicz, E.S. Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts 5-Bromoindole Aeromonas Caldariomyces Chloroperoxidase Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts Xanthomonas Bacteriology Biocatalysts Catalysis Chlorination Enzymes Bacteria chloride peroxidase chlorodimedone cyclohexanone derivative drug derivative halogenated hydrocarbon indole derivative indoline uracil article Ascomycetes bacterium biocatalysis enzymology halogenation metabolism Ascomycota Bacteria Biocatalysis Chloride Peroxidase Cyclohexanones Halogenation Hydrocarbons, Halogenated Indoles Uracil Aeromonas Citrobacter Leptoxyphium fumago Pseudomonas Streptomyces Xanthomonas 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. © 2011 Springer Science+Business Media B.V. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01415492_v33_n10_p1999_Medici |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts 5-Bromoindole Aeromonas Caldariomyces Chloroperoxidase Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts Xanthomonas Bacteriology Biocatalysts Catalysis Chlorination Enzymes Bacteria chloride peroxidase chlorodimedone cyclohexanone derivative drug derivative halogenated hydrocarbon indole derivative indoline uracil article Ascomycetes bacterium biocatalysis enzymology halogenation metabolism Ascomycota Bacteria Biocatalysis Chloride Peroxidase Cyclohexanones Halogenation Hydrocarbons, Halogenated Indoles Uracil Aeromonas Citrobacter Leptoxyphium fumago Pseudomonas Streptomyces Xanthomonas |
| spellingShingle |
Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts 5-Bromoindole Aeromonas Caldariomyces Chloroperoxidase Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts Xanthomonas Bacteriology Biocatalysts Catalysis Chlorination Enzymes Bacteria chloride peroxidase chlorodimedone cyclohexanone derivative drug derivative halogenated hydrocarbon indole derivative indoline uracil article Ascomycetes bacterium biocatalysis enzymology halogenation metabolism Ascomycota Bacteria Biocatalysis Chloride Peroxidase Cyclohexanones Halogenation Hydrocarbons, Halogenated Indoles Uracil Aeromonas Citrobacter Leptoxyphium fumago Pseudomonas Streptomyces Xanthomonas Médici, R. Garaycoechea, J.I. Dettorre, L.A. Iribarren, A.M. Lewkowicz, E.S. Biocatalysed halogenation of nucleobase analogues |
| topic_facet |
Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts 5-Bromoindole Aeromonas Caldariomyces Chloroperoxidase Enzymatic halogenation Haloperoxidases Nucleobases Whole cell biocatalysts Xanthomonas Bacteriology Biocatalysts Catalysis Chlorination Enzymes Bacteria chloride peroxidase chlorodimedone cyclohexanone derivative drug derivative halogenated hydrocarbon indole derivative indoline uracil article Ascomycetes bacterium biocatalysis enzymology halogenation metabolism Ascomycota Bacteria Biocatalysis Chloride Peroxidase Cyclohexanones Halogenation Hydrocarbons, Halogenated Indoles Uracil Aeromonas Citrobacter Leptoxyphium fumago Pseudomonas Streptomyces Xanthomonas |
| description |
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. © 2011 Springer Science+Business Media B.V. |
| format |
JOUR |
| author |
Médici, R. Garaycoechea, J.I. Dettorre, L.A. Iribarren, A.M. Lewkowicz, E.S. |
| author_facet |
Médici, R. Garaycoechea, J.I. Dettorre, L.A. Iribarren, A.M. Lewkowicz, E.S. |
| author_sort |
Médici, R. |
| title |
Biocatalysed halogenation of nucleobase analogues |
| title_short |
Biocatalysed halogenation of nucleobase analogues |
| title_full |
Biocatalysed halogenation of nucleobase analogues |
| title_fullStr |
Biocatalysed halogenation of nucleobase analogues |
| title_full_unstemmed |
Biocatalysed halogenation of nucleobase analogues |
| title_sort |
biocatalysed halogenation of nucleobase analogues |
| url |
http://hdl.handle.net/20.500.12110/paper_01415492_v33_n10_p1999_Medici |
| work_keys_str_mv |
AT medicir biocatalysedhalogenationofnucleobaseanalogues AT garaycoecheaji biocatalysedhalogenationofnucleobaseanalogues AT dettorrela biocatalysedhalogenationofnucleobaseanalogues AT iribarrenam biocatalysedhalogenationofnucleobaseanalogues AT lewkowiczes biocatalysedhalogenationofnucleobaseanalogues |
| _version_ |
1807317557347090432 |