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Enhanced Biocatalytic Performance of Bacterial Laccase from Streptomyces sviceus : Application in the Michael Addition Sequence Towards 3‐Arylated 4‐Oxochromanes
Author(s) -
Suljić Sanel,
Mortzfeld Frederik B.,
Gunne Matthias,
Urlacher Vlada B.,
Pietruszka Jörg
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500142
Subject(s) - laccase , biocatalysis , michael reaction , flow chemistry , chemistry , nucleophile , streptomyces , organic chemistry , combinatorial chemistry , sequence (biology) , catalysis , enzyme , reaction mechanism , bacteria , biochemistry , biology , genetics
A fast and efficient laccase‐catalysed oxidation/Michael addition sequence is performed using the bacterial laccase Ssl 1 from Streptomyces sviceus under basic conditions to provide a new class of 3‐arylated 4‐oxochromanes. This approach has advantages compared to previous biocatalytic arylation protocols that use fungal laccases under slightly acidic conditions to allow a significant decrease in reaction time with improved yields and maintained regio‐ and diastereoselectivity. Furthermore, a successful diastereoselective, consecutive one‐pot approach with the use of a hydrogenation flow system combined with the laccase‐catalysed arylation was performed. Finally, the general utility of this enzyme as a superior biocatalyst for Michael additions using several nucleophiles was demonstrated. The corresponding starting material was obtained in a straightforward esterification/hydrogenation process with the latter accomplished by using the flow system.