This title appears in the Scientific Report :
2015
Please use the identifier:
http://dx.doi.org/10.1002/cctc.201500142 in citations.
Enhanced Biocatalytic Performance of Bacterial Laccase from Streptomyces sviceus : Application in the Michael Addition Sequence Towards 3-Arylated 4-Oxochromanes
Enhanced Biocatalytic Performance of Bacterial Laccase from Streptomyces sviceus : Application in the Michael Addition Sequence Towards 3-Arylated 4-Oxochromanes
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 pro...
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Personal Name(s): | Suljić, Sanel |
---|---|
Mortzfeld, Frederik B. / Gunne, Matthias / Urlacher, Vlada B. / Pietruszka, Jörg (Corresponding author) | |
Contributing Institute: |
Institut für Bioorganische Chemie (HHUD); IBOC Biotechnologie; IBG-1 |
Published in: | ChemCatChem, 7 (2015) 8, S. 1380 - 1385 |
Imprint: |
Weinheim
WILEY-VCH Verlag
2015
|
DOI: |
10.1002/cctc.201500142 |
Document Type: |
Journal Article |
Research Program: |
Biotechnology |
Publikationsportal JuSER |
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. |