Synthesis of Dihydroxyacetone Phosphate (and Isosteric Analogues) by Enzymatic Oxidation; Sugars from Glycerol

Authors

  • Prof. Dr. Wolf-Dieter Fessner,

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    1. Institut für Organische Chemie und Biochemie der Universität, Albertstrasse 21, D-79104 Freiburg (FRG)
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    1. Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-52056 Aachen (FRG), Telefax: Int. code +(241)8888-127
    • Institut für Organische Chemie und Biochemie der Universität Albertstrasse 21, D-79104 Freiburg (FRG)
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  • Dipl.-Chem. Gudrun Sinerius

    1. Institut für Organische Chemie und Biochemie der Universität, Albertstrasse 21, D-79104 Freiburg (FRG)
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  • Enzymes in Organic Synthesis, Part 7. This research was supported by the Deutsche Forschungsgemeinschaft (Grant Fe 244/2-2), the Fonds der Chemischen Industrie, and the Wissenschaftliche Gesellschaft Freiburg. We thank Dr. P. Rasor, Boehringer Mannheim GmbH, for the generous gift of several enzymes, and Dr. W. Deck for 31P NMR spectra.—Part 6: [3b].

Abstract

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The combination of enzymes glycerol phosphate oxidase and catalase allows the efficient preparative oxidation of glycerol phosphate 1 (X = O) with elemental oxygen which yields dihydroxyacetone phosphate 2 (X = O). Phosphate 2 can be added to various aldehydes in a one-flask, enzyme-catalyzed reaction to furnish 3 (X = O). Isosteric analogues of glycerol phosphate 1 (X = CH2, NH, S) can be converted into the corresponding adducts 3.

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