Enzymatic Desymmetrisation of Prochiral

Herein we present the biocatalysed preparation of a mono-N-carbamate-protected precursor of antitumoral Nutlin-3a through enantioselective alkoxycarbonylation of meso-1,2-disubstituted-1,2-diaminoethane using enzyme lipases and dialkyl carbonates as acylating agents. A series of supported or free li...

Full description

Bibliographic Details
Published in:Molecules
Main Authors: Cristofori, Virginia, Illuminati, Davide, Bisquoli, Chiara, Catani, Martina, Compagnin, Greta, Turrin, Giulia, Trapella, Claudio, Fantinati, Anna
Format: Article in Journal/Newspaper
Language:English
Published: MDPI 2024
Subjects:
Nutlin-3a
biocatalysis
desymmetrisation
vicinal meso-diamines
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/molecules29143267
https://pubmed.ncbi.nlm.nih.gov/39064846
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11279714/
Description
Summary:Herein we present the biocatalysed preparation of a mono-N-carbamate-protected precursor of antitumoral Nutlin-3a through enantioselective alkoxycarbonylation of meso-1,2-disubstituted-1,2-diaminoethane using enzyme lipases and dialkyl carbonates as acylating agents. A series of supported or free lipase enzymes were screened in combination with commercially available diallyl, diethyl and dimethyl carbonates. The reactions were conducted at different temperatures, for different reaction times and with variable co-solvent systems to evaluate the effects on the enzyme catalytic activity. The best results in terms of conversion, enantiomeric excess and yield were obtained when lipase from Candida antarctica B (CAL-B) was used with diallyl carbonate (DAC) when conducting the reaction solventless at 75 °C.

Similar Items