Universität zu Köln

Hilken, Stefan, Kaletta, Florian, Heinsch, Angela, Neudoerfl, Joerg-M. and Berkessel, Albrecht ORCID: 0000-0003-0470-7428 (2014). Synthesis of an Oxidation-Stable Analogue of Cyclic Pyranopterin Monophosphate ( cPMP). Eur. J. Org. Chem., 2014 (11). S. 2231 - 2242. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

Molybdenum cofactor (Moco) deficiency is a lethal hereditary metabolic disease. A recently developed therapy requires continuous intravenous supplementation of the biosynthetic Moco precursor cyclic pyranopterin monophosphate (cPMP). The limited stability of the latter natural product, mostly due to oxidative degradation, is problematic for oral administration. Therefore, the synthesis of more stable cPMP analogues is of great interest. In this context and for the first time, the synthesis of a cPMP analogue, in which the oxidation-labile reduced pterin unit is replaced by a pyrazine moiety, was achieved starting from the chiral pool materials D-galactose or D-arabitol. Our synthesis, 13 steps in total, includes the following key transformations: i) pyrazine lithiation, followed by acylation; ii) closure of the pyrane ring by nucleophilic aromatic substitution; and iii) introduction of phosphate.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Hilken, Stefan UNSPECIFIED UNSPECIFIED UNSPECIFIED Kaletta, Florian UNSPECIFIED UNSPECIFIED UNSPECIFIED Heinsch, Angela UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-441683
DOI:	10.1002/ejoc.201301784
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2014
Number:	11
Page Range:	S. 2231 - 2242
Date:	2014
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
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 MOLYBDENUM COFACTOR BIOSYNTHESIS; DIRECT CONVERSION; MOLYBDOPTERIN; IDENTIFICATION; INTERMEDIATE; METALATION; TUNGSTEN; ENZYMES; BIOLOGY; SYSTEM Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/44168