Enzymatic resolution of hindered cyanohydrins, key precursors of muscarinic receptor antagonists
| Autor: | Vicente Gotor-Fernández, Verónica Recuero, Rosario Brieva, Vicente Gotor, Miguel Ferrero |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
biology
Molecular model Stereochemistry Organic Chemistry Substrate (chemistry) biology.organism_classification Phosphonate Catalysis Inorganic Chemistry Acylation Hydrolysis chemistry.chemical_compound chemistry Transition state analog Enzymatic hydrolysis Candida antarctica Physical and Theoretical Chemistry |
| Zdroj: | Tetrahedron: Asymmetry. 18:994-1002 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2007.04.002 |
| Popis: | Enantiomerically pure 1-cycloalkyl-1-hydroxy-1-phenylcyanohydrins, key precursors in the synthesis of ( S )-oxybutynin and other antimuscarinic agents, have been successfully prepared via lipase-catalyzed kinetic resolutions. Pseudomonas cepacia and Candida antarctica lipase B have shown excellent enantioselectivities in hydrolysis and acylation processes, depending on the substrate structure and the reaction conditions. Furthermore, molecular modeling of phosphonate transition state analogue for the C. antarctica lipase B enzymatic hydrolysis resolution step supports these facts, which were experimentally observed. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect