Universität zu Köln

Griesbeck, Axel G. ORCID: 0000-0002-6546-3482, Kleczka, Margarethe, de Kiff, Alan, Vollmer, Moritz, Eske, Angelika and Sillner, Sarah (2015). Singlet oxygen and natural substrates: functional polyunsaturated models for the photooxidative degradation of carotenoids. Pure Appl. Chem., 87 (7). S. 639 - 648. BERLIN: WALTER DE GRUYTER GMBH. ISSN 1365-3075

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Abstract

The primary chemical reactions of singlet molecular oxygen with polyunsaturated carotenoids are the focus of this research report. Model compounds that exhibit electronic properties and substituent pattern similar to natural carotenes, xanthophylls or apocarotenoids, respectively, were investigated with regard to photooxygenation reactivity. For dienes and trienes as substrates, high tandem reactivity was observed and hydroperoxy-endoperoxides were isolated as the secondary products of singlet oxygen reaction. The electronic gem-effect on the regioselectivity of the ene reaction is conserved also in vinylogous positions and thus appears to originate from a radical-stabilizing effect. In an attempt to combine different peroxide groups derived from natural products as a tool for new pharmaceutically active products, a dyade synthesis of an artemisinine-safranol with subsequent singlet oxygen addition was realized.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Griesbeck, Axel G. UNSPECIFIED orcid.org/0000-0002-6546-3482 UNSPECIFIED Kleczka, Margarethe UNSPECIFIED UNSPECIFIED UNSPECIFIED de Kiff, Alan UNSPECIFIED UNSPECIFIED UNSPECIFIED Vollmer, Moritz UNSPECIFIED UNSPECIFIED UNSPECIFIED Eske, Angelika UNSPECIFIED UNSPECIFIED UNSPECIFIED Sillner, Sarah UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-399582
DOI:	10.1515/pac-2015-0209
Journal or Publication Title:	Pure Appl. Chem.
Volume:	87
Number:	7
Page Range:	S. 639 - 648
Date:	2015
Publisher:	WALTER DE GRUYTER GMBH
Place of Publication:	BERLIN
ISSN:	1365-3075
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ENE-REACTION; BETA-CAROTENE; PHOTOSYSTEM-II; RATE CONSTANTS; MOLECULAR-OXYGEN; HYBRID MOLECULES; AQUEOUS-SOLUTION; ACTIVE COMPOUNDS; PHOTOOXYGENATION; ARTEMISININ Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/39958