Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4 (Articolo in rivista)

Type
Label
  • Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4 (Articolo in rivista) (literal)
Anno
  • 2010-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetasy.2010.04.022 (literal)
Alternative label
  • D'Antona N.; Nicolosi G.; Morrone R.; Kubác¡ D.; Kaplan O.; Martínková L. (2010)
    Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • D'Antona N.; Nicolosi G.; Morrone R.; Kubác¡ D.; Kaplan O.; Martínková L. (literal)
Pagina inizio
  • 695 (literal)
Pagina fine
  • 702 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.sciencedirect.com/science/article/pii/S0957416610002697 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 21 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 8 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 6 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Chimica Biomolecolare del CNR--UOS Catania Laboratory of Biotransformation, Institute of Microbiology of the Academy of Sciences of the Czech Republic (literal)
Titolo
  • Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4 (literal)
Abstract
  • A variety of novel cyano-cyclitols possessing complex stereochemistry have been synthesized. These compounds were subjected to the biocatalyzed hydrolysis of their nitrile groups. The bacterial strain Rhodococcus erythropolis A4, expressing a nitrile hydratase/amidase bienzymatic system, was able to recognize (1R,2S,3S,4R)/(1S,2R,3R,4S)-1-cyano-2,3,4-trihydroxy-cyclohex-5-ene and trans-3-cyanocyclohexa- 3,5-diene-1,2-diol, and to catalyze their transformations into the corresponding amides and acids. The kinetic and stereochemical trends of these biotransformations, a rare example of the enantiorecognition of a rigid bulky aliphatic substrate, are discussed. (literal)
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