“Artificial Metabolisms” for the Asymmetric One-Pot Synthesis of Branched-Chain Saccharides

Authors

  • Dr. Wolf-Dieter Fessner,

    Corresponding author
    1. Institut für Organische Chemie und Biochemie der Universität, Albertstrasse 21, D-W-7800 Freiburg (FRG)
    • Institut für Organische Chemie und Biochemie der Universität, Albertstrasse 21, D-W-7800 Freiburg (FRG)
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  • Christiane Walter

    1. Institut für Organische Chemie und Biochemie der Universität, Albertstrasse 21, D-W-7800 Freiburg (FRG)
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  • Enzymes in Organic Synthesis, Part 3. This research was supported by the Deutsche Forschungsgemeinschaft (Grant Fe 244/2–1), the Wissenschaftliche Gesellschaft Freiburg, and the Fonds der Chemischen Industrie. The generous gift of recombinant bacterial strains by Prof. Dr. D. G. Fraenkel, Harvard Medical School, Boston, is gratefully acknowledged. We thank Dipl.-Chem. O. Eyrisch and Dipl.-Chem. G. Sinerius for samples of purified PFK-2 from E. coli and 7, respectively.—Part 2: [3b].

  • Dedicated to Professor George A. Olah on the occasion of his 65th birthday

Abstract

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The renewable resources glucose, fructose, and sucrose are rendered useful sources of dihydroxyacetonephosphate (DHAP) for asymmetric aldol additions by multienzymatic reaction cascades in vitro with the rabbit muscle aldoase (FruA). In highly diastereoselective, efficient transformations with aldehydes, a series of unusual alkylated spiroannelated and branched saccharides become accessible (E = enzyme).

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