Dissertation / PhD Thesis/Book

PreJuSER-51186

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Chemoenzymatische Synthese $\alpha,\beta$-propargylischer Alkohole

Schubert, T. (Corresponding author)FZJ*

2002
Forschungszentrum Jülich GmbH Zentralbibliothek, Verlag Jülich

Please use a persistent id in citations: http://hdl.handle.net/2128/113

Report No.: Juel-3983

Abstract: This study describes the use of oxidoreductases for the reduction of propargylic ketones. In this first comprehensive investigation of the enzymatic reduction of alkynones a total of more than 50 substrates were prepared and tested. It was possible to make enantiomerically pure (R)- and (S)-methyl-ethinyl-carbinois with widely differing residues at the triple bond almost universally accessible via recLB-ADH and CPCR. The reduction of propargylic ketones with a terminal triple bond by means of recLB-ADH led to an inversion of the configuration of the alcohols obtained. $\alpha$-chlorinated and $\alpha$-brominated alkynones were reduced to the corresponding halogenated alcohols via the enzymes recLB-ADH, HL-ADH and TB-ADH with high activities. The enzymatic reduction was optimized for the multifunctional chlorinated C4 constituents. The substrates were quantitatively reduced an the mmole scale with cofactor TTNs of up to 20,000. In conclusion, the versatile consecutive chemistry of the halogenated propargylic alcohols was demonstrated by transforming them into epoxides, nitriles and olefins.

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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