Sie befinden Sich nicht im Netzwerk der Universität Paderborn. Der Zugriff auf elektronische Ressourcen ist gegebenenfalls nur via VPN oder Shibboleth (DFN-AAI) möglich. mehr Informationen...
Desymmetric hydrolysis of prochiral imide for S -pregabalin synthesis by rationally designed d -hydantoinase
Ist Teil von
Green chemistry : an international journal and green chemistry resource : GC, 2022-06, Vol.24 (12), p.4748-4753
Ort / Verlag
Cambridge: Royal Society of Chemistry
Erscheinungsjahr
2022
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
S -Pregabalin ( S -PGB) is an effective medicine for analgesic, anticonvulsant and anxiolytic treatments. To date, enantioselective synthesis of S -PGB suffers from 50% undesired by-product that needs to be recycled via highly polluting chemical processes. In this study, we rationally engineered d -hydantoinase to desymmetrize prochiral 3-isobutyl glutarimide to yield R -3-isobutyl glutaric acid monoamide ( R -IBM), the direct chiral precursor for S -PGB. The best variant (M63AL65HC317T) could produce R -IBM with great overall conversion (99% molar yield) and a high ee p value (99.8%) in a kilogram scale synthesis. This study offers a novel green and atom-efficient route for S -PGB production.