Universität zu Köln

Lim, David ORCID: 0000-0002-7149-6459, Griindemann, Dirk and Seebeck, Florian P. (2019). Total Synthesis and Functional Characterization of Selenoneine. Angew. Chem.-Int. Edit., 58 (42). S. 15026 - 15031. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

The N-alpha-trimethyl 2-selenohistidine selenoneine is the selenium isolog of the natural antioxidant ergothioneine. Sulfur-to-selenium substitutions are known to endow proteins and nucleic acids with special activities. In contrast, secondary metabolites that exploit selenium-specific chemistry are rare. Selenoneine therefore provides a unique opportunity to study how natural organoselenides interact with cellular processes. In this report we describe the chemical synthesis of selenoneine and other 2-selenoimidazoles. With synthetic selenoneine at hand we discovered a set of reactivities that distinguish selenoneine from ergothioneine, showing that the two compounds can fill distinct functional niches. Synthetic access to 2-selenoimidazoles should pave the way to explore the pharmaceutical potential and physiological function of this heretofore inaccessible class of compounds.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Lim, David UNSPECIFIED orcid.org/0000-0002-7149-6459 UNSPECIFIED Griindemann, Dirk UNSPECIFIED UNSPECIFIED UNSPECIFIED Seebeck, Florian P. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-141608
DOI:	10.1002/anie.201908967
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	58
Number:	42
Page Range:	S. 15026 - 15031
Date:	2019
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3773
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SELENIUM-CONTAINING COMPOUND; CONTAINING AMINO-ACIDS; STRUCTURAL-CHARACTERIZATION; ANTITHYROID DRUGS; ORGANOSELENIUM COMPOUNDS; ORGANIC SELENIUM; PROTECTING-GROUP; L-ERGOTHIONEINE; DOUBLE-BLIND; EBSELEN Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/14160