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Biocatalytic Approaches to the Enantiomers of Wieland–Miescher Ketone and its Derivatives
Author(s) -
Bertuletti Susanna,
Bayout Ikram,
Bassanini Ivan,
Ferrandi Erica E.,
Bouzemi Nassima,
Monti Daniela,
Riva Sergio
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100174
Subject(s) - kinetic resolution , chemistry , ketone , diastereomer , enantiomer , lipase , acetone , alcohol , organic chemistry , acetylation , biocatalysis , enantioselective synthesis , stereochemistry , enzyme , catalysis , biochemistry , reaction mechanism , gene
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 Dm7α‐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.