Data di Pubblicazione:
2018
Citazione:
A biocatalytic approach to the synthesis of pharmacologically active compounds / S. Ciceri, B. Guidi, S. Reza Elahi, P. Ferraboschi. ((Intervento presentato al convegno Workshop BIOMETRA tenutosi a Segrate nel 2018.
Abstract:
Several pharmacologically active compounds present in their structure different functional groups and
stereocenters so, for their synthesis, chemo-, regio-, stereoselective transformations are required. This
selectivity can be achieved using biocatalysts (enzymes and microorganisms).
The aim of our work is the preparation of some pharmacologically active compounds using biocatalytic
methodologies which can lead to important improvements compared to traditional approaches, such as
better yields and shorter synthetic pathways. Moreover the use of biocatalysts in synthesis is a green
approach.
For example, in our laboratory through a regioselective transformation catalysed by an enzyme, Alcalase
CLEA, we have achieved the synthesis of capecitabine (Xeloda), an antitumor with a nucleosidic scaffold.
After the investigation of the activity of different enzymes and microorganisms we have obtained both the
enantiomerically pure synthons for the preparation of (S)-pramipexole, a synthetic dopaminergic agonist
utilized as anti-Parkinson agent, and (R)-pramipexole, which has been studied for the treatment of
amyotrophic lateral sclerosis (ALS).
Through a similar biocatalytic approach is under development the synthesis of brivaracetam, a novel
anticonvulsant drug. The crucial step of the synthesis of this molecule is the obtainment of the
stereocenter bearing the propyl moiety with the proper configuration.
This aim was achieved by means of a lipase-catalysed resolution of the suitable precursor of the finale
molecule.
Tipologia IRIS:
14 - Intervento a convegno non pubblicato
Keywords:
Biocatalysis, Enzymes, Baker’s Yeast, Regioselectivity, Stereoselectivity
Elenco autori:
S. Ciceri, B. Guidi, S. Reza Elahi, P. Ferraboschi
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