Dissertation / PhD Thesis/Book

PreJuSER-51173

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Funktionalisierte Cyclohexadien-trans-1,2-diole : Zugang durch Techniken des metabolic engineering und Verwendung als Bausteine in der Naturstoff- und Wirkstoffsynthese

Franke, D. (Corresponding author)FZJ*

2002
Forschungszentrum Jülich GmbH Zentralbibliothek, Verlag Jülich

Please use a persistent id in citations: http://hdl.handle.net/2128/111

Report No.: Juel-3992

Abstract: Within the last years functionalized cyclohexadiene-$\textit{trans}$-1,2-diols ($\textit{trans}$-CHD) have been suggested to be potential starting material for the synthesis of a vast variety of bioactive substances, especially in the chemistry of carbohydrate mimetics. By homologous expression of the genes encoding for isochorismate synthase EntC and isochorismatase EntB in $\textit{E. coli}$ mutants with deficiencies in the chorismate dependent pathways, microbial systems could be obtained, which enable the enantioselective production of two $\textit{trans}$-CHD, (2S,3S)-dihydroxy-dihydrobenzoic acid (2,3-$\textit{trans}$-CHD) and (3R,4R)- dihydroxy-dihydrobenzoic acid (3,4-$\textit{trans}$-CHD), starting from glucose and other renewable carbon-sources. [Abb.] Microbially produced $\textit{trans}$-CHD have been characterized to be highly thermostable in contrast to chorismate and isochorismate, because no enolpyruvoyl residue enables the aromatization reaction via pericyclic transition states. Making use of the carboxylic acid functionality the $\textit{trans}$-CHD can be isolated selectively with 96 % purity and 75 % yield by ion exchange chromatography or, alternatively, by extraction. [Abb.] Starting from enantiomerically pure 2,3-$\textit{trans}$-CHD synthetic routes towards acceptor and donor building blocks for the synthesis of pseudooligosaccharids with acarviosin substructure were developed, including the first synthesis of an analogue of the pharmacologically interesting carbohydrate mimetic tri-$\textit{epi}$-valienamine and the formal synthesis of $\textit{ent}$-valienamine. With the preparative access to these building blocks the applicability of $\textit{trans}$-CHD as synthetic building blocks in bioactive substance syntheses has been demonstrated.

Note: Record converted from VDB: 12.11.2012
Note: Bonn, Univ., Diss., 2002

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Contributing Institute(s):

1. Biotechnologie 2 (IBT-2)

Research Program(s):

1. Biotechnologie (L02)

Appears in the scientific report 2002

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Database coverage:

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