Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic Biosynthesis Studies

Title data

Wunderlich, Johannes ; Roß, Theresa ; Schröder, Marius ; Hahn, Frank:
Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic Biosynthesis Studies.
In: Organic Letters. Vol. 22 (2020) Issue 13 . - pp. 4955-4959.
ISSN 1523-7052
DOI: https://doi.org/10.1021/acs.orglett.0c01348

Official URL:

Abstract in another language

Studies on the biosynthetic processing of polyene thioester intermediates are complicated by limited access to appropriate substrate surrogates. We present a step-economic synthetic access to biomimetic β-ketopolyene thioesters that is based on an Ir-catalyzed reductive Horner–Wadsworth–Emmons olefination. New β-ketotriene and pentaenethioates of pantetheine and N-acetylcysteamine were exemplarily synthesized via short and concise routes. The usefulness of these compounds was demonstrated in an in vitro assay with the ketoreductase domain MycKRB from mycolactone biosynthesis.

Further data

Item Type:	Article in a journal
Refereed:	Yes
Institutions of the University:	Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry - Food Chemistry > Professor Organic Chemistry - Food Chemistry - Univ.-Prof. Dr. Frank Hahn Profile Fields > Emerging Fields > Food and Health Sciences Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry - Food Chemistry Profile Fields Profile Fields > Emerging Fields
Result of work at the UBT:	Yes
DDC Subjects:	500 Science > 540 Chemistry
Date Deposited:	25 Jun 2020 06:54
Last Modified:	05 Apr 2022 06:40
URI:	https://eref.uni-bayreuth.de/id/eprint/55614