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Chemoenzymatic synthesis of levetiracetam and analogues

Grant number: 13/16636-1
Support type:Scholarships in Brazil - Master
Effective date (Start): November 01, 2013
Effective date (End): February 28, 2015
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Cintia Duarte de Freitas Milagre
Grantee:Bruno Sérgio Do Amaral
Home Institution: Instituto de Química (IQ). Universidade Estadual Paulista (UNESP). Campus de Araraquara. Araraquara , SP, Brazil

Abstract

Biocatalysts (enzymes and / or microorganisms) are widely used to create or resolve chiral centers, especially for drug synthesis. Levetiracetam (LEV), commercially known as Keppra®, is a chiral substance with anticonvulsant properties whose pharmacological activity is related to its (S) enantiomer. The increase of LEV usage over other anticonvulsant drugs is closely associated with its low occurrence of side effects. Several routes for LEV chemosynthetic production are reported in the literature. Most of them involve numerous synthetic steps, high-energy consumption, use of metal catalysts and low overall yields. On the other hand, this project aims to develop a chemoenzymatic route, with fewer steps, milder conditions and environmentally friendly reaction for the synthesis of LEV and analogues. The first step will focus on the synthesis of butanecyanohydrin from cyanosilylation of propanal, followed by the formation of halogenated compound. Different nitrogen heterocycles will replace the halogen atom to produce the starting materials for microbial enzymatic reactions. The main strategies to obtain the desired products, with high yields and enantioselectivity, will be the enzymatic selection and screening and use of ionic liquids as reaction medium.

Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
AMARAL, Bruno Sérgio Do. Síntese quimioenzimática do levetiracetam e análogos. 2015. 212 f. Master's Dissertation - Universidade Estadual Paulista "Júlio de Mesquita Filho" Instituto de Química..

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