Many pharmaceutically active compounds contain a chiral core inside their structure. The required chemo-, regio-, and stereo-selectivity can be achieved using biocatalysts (enzymes or microorganisms), which transform a wide range of substrates under mild reaction conditions. Our research work focuses on the biocatalytic synthesis of key building blocks of active pharmaceutical ingredients. In this communication, two examples of this approach will be described: the synthesis of the enantiopure key intermediates of brivaracetam and pramipexole. I) Brivaracetam is a recently approved anticonvulsant drug. The crucial step in the synthetic pathway of this drug is the obtainment of the precursor (R)-4-propyldihydrofuran-2(3H)-one, bearing the propyl moiety essential for its pharmacological activity. We achieved this enantiomerically pure intermediate through a convenient biocatalytic approach. II) For the preparation of (S)-pramipexole, a dopaminergic agonist employed as anti-Parkinson agent, and (R)-pramipexole, a potential treatment for eosinophilic asthma and hypereosinophilic syndrome, we investigated the activity and selectivity of different microorganisms (mainly yeasts). This approach allowed us to obtain enantiomerically pure synthons, but now we improved our previous results using enzymes as biocatalysts, i.e. lipases in organic solvents.

Biocatalysts for the synthesis of pharmacologically active compounds / S. Ciceri, P. Grisenti, F. Meneghetti, M. Mori, S. Reza Elahi, P. Ferraboschi. ((Intervento presentato al convegno SCI - ViSYOChem tenutosi a online nel 2020.

Biocatalysts for the synthesis of pharmacologically active compounds

S. Ciceri
;
F. Meneghetti;M. Mori;P. Ferraboschi
2020-11-06

Abstract

Many pharmaceutically active compounds contain a chiral core inside their structure. The required chemo-, regio-, and stereo-selectivity can be achieved using biocatalysts (enzymes or microorganisms), which transform a wide range of substrates under mild reaction conditions. Our research work focuses on the biocatalytic synthesis of key building blocks of active pharmaceutical ingredients. In this communication, two examples of this approach will be described: the synthesis of the enantiopure key intermediates of brivaracetam and pramipexole. I) Brivaracetam is a recently approved anticonvulsant drug. The crucial step in the synthetic pathway of this drug is the obtainment of the precursor (R)-4-propyldihydrofuran-2(3H)-one, bearing the propyl moiety essential for its pharmacological activity. We achieved this enantiomerically pure intermediate through a convenient biocatalytic approach. II) For the preparation of (S)-pramipexole, a dopaminergic agonist employed as anti-Parkinson agent, and (R)-pramipexole, a potential treatment for eosinophilic asthma and hypereosinophilic syndrome, we investigated the activity and selectivity of different microorganisms (mainly yeasts). This approach allowed us to obtain enantiomerically pure synthons, but now we improved our previous results using enzymes as biocatalysts, i.e. lipases in organic solvents.
Biocatalysis; Saccharomyces cerevisiae; Enzymes; Lipases; Pramipexole; Brivaracetam; Kinetic resolution; Asymmetric synthesis
Settore CHIM/06 - Chimica Organica
Settore BIO/10 - Biochimica
Settore CHIM/08 - Chimica Farmaceutica
https://scivisyochem2020.weebly.com/
Biocatalysts for the synthesis of pharmacologically active compounds / S. Ciceri, P. Grisenti, F. Meneghetti, M. Mori, S. Reza Elahi, P. Ferraboschi. ((Intervento presentato al convegno SCI - ViSYOChem tenutosi a online nel 2020.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/784649
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