Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

0350832 - MBÚ 2011 RIV GB eng J - Článek v odborném periodiku
D’Antona, N. - Nicolosi, G. - Morrone, R. - Kubáč, David - Kaplan, Ondřej - Martínková, Ludmila
Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4.
Tetrahedron Asymmetry. Roč. 21, č. 6 (2010), s. 695-702. ISSN 0957-4166
Grant CEP: GA MŠMT OC09046
Výzkumný záměr: CEZ:AV0Z50200510
Klíčová slova: ALICYCLIC NITRILES * ASYMMETRIZATION * HYDROLYSIS
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.484, rok: 2010

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
Trvalý link: http://hdl.handle.net/11104/0190727