This title appears in the Scientific Report :
2014
Please use the identifier:
http://hdl.handle.net/2128/8293 in citations.
2-Steps in 1-pot: enzyme cascades for the synthesis of chiral vicinal amino alcohols
2-Steps in 1-pot: enzyme cascades for the synthesis of chiral vicinal amino alcohols
Amino alcohols, and especially nor(pseudo)ephedrines, are compounds with variousapplications in organic synthesis and in the pharmaceutical industry. The strategiesto these chiral molecules by classical chemical or chemo-enzymatical syntheses arechallenging and therewith draw interest for industrial...
Saved in:
Personal Name(s): | Sehl, Torsten (Corresponding author) |
---|---|
Contributing Institute: |
Biotechnologie; IBG-1 |
Published in: | 2014 |
Imprint: |
Jülich
Forschungszentrum Jülich GmbH Zentralbibliothek, Verlag
2014
|
Physical Description: |
XIV, 167 S. |
Dissertation Note: |
Dissertation, Heinrich-Heine-Universität Düsseldorf, 2014 |
ISBN: |
978-3-95806-001-2 |
Document Type: |
Book Dissertation / PhD Thesis |
Research Program: |
ohne Topic |
Series Title: |
Schriften des Forschungszentrums Jülich. Reihe Schlüsseltechnologien / Key Technologies
95 |
Subject (ZB): | |
Link: |
OpenAccess |
Publikationsportal JuSER |
Amino alcohols, and especially nor(pseudo)ephedrines, are compounds with variousapplications in organic synthesis and in the pharmaceutical industry. The strategiesto these chiral molecules by classical chemical or chemo-enzymatical syntheses arechallenging and therewith draw interest for industrial research efforts. In this thesis,the potential of enzyme cascades for the synthesis of chiral primary vicinal aminoalcohols was demonstrated. In detail, the 2-step cascades combining thiaminediphosphate (ThDP)-dependent enzymes and ω-transaminases were investigated forthe synthesis of nor(pseudo)ephedrines. This approach represents a completely newstrategy for getting access to chiral amino alcohols. These valuable chemicals arenow accessible in a highly atom- and step-efficient enzymatic process in only tworeaction steps from inexpensive, achiral starting materials. $\underline{Development}$ $\underline{of}$ $\underline{a}$ $\underline{novel}$ $\underline{screening}$ $\underline{assay}$ $\underline{for}$ $\underline{ω-transaminases}$ In the developed synthetic enzyme cascade, amino alcohols are accessible via a carboligation of aldehydes and α-keto acids, followed by a subsequent reductive amination of the α-hydroxy ketone intermediate catalysed by ω-transaminases. For a fast and reliable screening of ω-transaminase activity in these reductive amination reactions, a novel screening assay was developed. This assay is meanwhile used by other working groups and companies to screen enzymatic reductive amination reactions. Using this assay, we identified valuable biocatalysts for the reductive amination of acetoin, 2-hydroxyacetophenone and phenylacetylcarbinol (PAC). The reductive amination of PAC was of special importance, since is the reaction intermediate in the 2-step cascade for the synthesis of nor(pseudo)ephedrines. $\underline{1-Pot}$ $\underline{2-step}$ $\underline{cascade}$ $\underline{combining}$ $\underline{ThDP-dependent}$ $\underline{enzymes}$ $\underline{and}$ $\underline{ω-transaminases}$ [...] |