Biocatalytic Approaches to the Enantiomers of Wieland–Miescher Ketone and its Derivatives

Autor:	Sergio Riva, Erica Elisa Ferrandi, Ivan Bassanini, Daniela Monti, Ikram Bayout, Nassima Bouzemi, Susanna Bertuletti
Rok vydání:	2021
Předmět:	chemistry.chemical_compound chemistry Wieland-Miescher ketone Biocatalysis Organic Chemistry Organic chemistry Lipases Wieland–Miescher ketone Physical and Theoretical Chemistry Enantiomer Dehydrogenases Enzymes
Zdroj:	European journal of organic chemistry (Online) (2021). doi:10.1002/ejoc.202100174 info:cnr-pdr/source/autori:Bertuletti S.; Bayout I.; Bassanini I.; Ferrandi E.E.; Bouzemi N.; Monti D.; Riva S./titolo:Biocatalytic Approaches to the Enantiomers of Wieland-Miescher Ketone and its Derivatives/doi:10.1002%2Fejoc.202100174/rivista:European journal of organic chemistry (Online)/anno:2021/pagina_da:/pagina_a:/intervallo_pagine:/volume
ISSN:	1099-0690 1434-193X
Popis:	Biocatalytic approaches have been investigated in order to isolate the enantiomers of Wieland-Miescher ketone (1) and of its alcoholic derivatives (cis-2 and trans-3). Specifically, two enzymes from our in-house metagenomic collection of oxidoreductases, IS2-SDR and Dm7?-HSDH, catalyzed the kinetic resolution of the starting racemic ketone 1 or its complete conversion into two diastereomeric products, respectively. Moreover, the kinetic resolution of the racemic cis-alcohol (2) was very efficiently obtained (E?2.000) by lipase PS catalyzed acetylation in dry acetone. All the products were isolated with ee>=95 %. Simple chemical elaborations of some of them allowed to isolate the missing enantiomers.
Databáze:	OpenAIRE
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