Journal Article

FZJ-2019-00483

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Tyrosinases in Organic Chemistry: A Versatile Tool for the α-Arylation of β-Dicarbonyl Compounds

Krug, R.RWTH* ; Schröder, D.FZJ* ; Gebauer, J.FZJ* ; Suljic, S. ; Morimoto, Y. ; Fujieda, N. ; Itoh, S. ; Pietruszka, J. (Corresponding author)FZJ*

2018
Wiley-VCH Verl. Weinheim

This record in other databases:    

Please use a persistent id in citations: doi:10.1002/ejoc.201800188

Abstract: 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.

---

Contributing Institute(s):

1. Institut für Bioorganische Chemie (HHUD) (IBOC)
2. Biotechnologie (IBG-1)

Research Program(s):

1. 581 - Biotechnology (POF3-581) (POF3-581)

Appears in the scientific report 2018

---

Database coverage:
; Clarivate Analytics Master Journal List ; Current Contents - Physical, Chemical and Earth Sciences ; Ebsco Academic Search ; IF < 5 ; JCR ; NCBI Molecular Biology Database ; SCOPUS ; Science Citation Index ; Science Citation Index Expanded ; Web of Science Core Collection

---