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Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4
- 1.0350832 - MBÚ 2011 RIV GB eng J - Journal Article
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
R&D Projects: GA MŠMT OC09046
Institutional research plan: CEZ:AV0Z50200510
Keywords : ALICYCLIC NITRILES * ASYMMETRIZATION * HYDROLYSIS
Subject RIV: CC - Organic Chemistry
Impact factor: 2.484, year: 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
Permanent Link: http://hdl.handle.net/11104/0190727
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