This title appears in the Scientific Report :
2018
Please use the identifier:
http://dx.doi.org/10.1002/ejoc.201800188 in citations.
Tyrosinases in Organic Chemistry: A Versatile Tool for the α-Arylation of β-Dicarbonyl Compounds
Tyrosinases in Organic Chemistry: A Versatile Tool for the α-Arylation of β-Dicarbonyl Compounds
A tyrosinase‐mediated arylation towards a variety of different building blocks is presented. Utilizing phenol or simple substituted phenols, the corresponding quinones are synthesized in a two‐step procedure by an enzyme‐catalyzed oxidation (tyrosinase from Aspergillus oryzae). The activated interme...
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Personal Name(s): | Krug, Roxanne |
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Schröder, Dennis / Gebauer, Jan / Suljic, Sanel / Morimoto, Yuma / Fujieda, Nobutaka / Itoh, Shinobu / Pietruszka, Jörg (Corresponding author) | |
Contributing Institute: |
Biotechnologie; IBG-1 Institut für Bioorganische Chemie (HHUD); IBOC |
Published in: | European journal of organic chemistry, 2018 (2018) 15, S. 1789 - 1796 |
Imprint: |
Weinheim
Wiley-VCH Verl.
2018
|
DOI: |
10.1002/ejoc.201800188 |
Document Type: |
Journal Article |
Research Program: |
Biotechnology |
Publikationsportal JuSER |
A tyrosinase‐mediated arylation towards a variety of different building blocks is presented. Utilizing phenol or simple substituted phenols, the corresponding quinones are synthesized in a two‐step procedure by an enzyme‐catalyzed oxidation (tyrosinase from Aspergillus oryzae). The activated intermediates undergo a 1,4‐addition with selected β‐dicarbonyl compounds. Starting from phenol, yields of isolated product for the hydroxylation‐oxidation‐arylation sequence range from 43–77 %, whereas substituted acceptors provided 9–55 %, only. Different substitution patterns on phenol revealed that electron donating functionalities are preferentially accepted to electron withdrawing ones, whereas ortho‐substituted phenols are not accepted at all. |