- Enzymes in Organic Synthesis, 11. Expedient Enantioselective Synthesis of (S)-(-)-3,4-Dihydroxybutylphosphonate, an Isosteric Substrate Mimic for Glycerol Phosphate Oxidase
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The title compound (S)-(-)-2 was obtained in enantiomerically pure form and 47percent overall yield starting from (S)-malic acid (S)-7 by a 5-step sequence involving reduction to (S)-1,2,4-butanetriol (S)-8, acetalization, and introduction of the phosphonate group by an Arbusow reaction.Compound (S)-(-)-2 is a substrate for the L-glycerol 3-phosphate oxidase from Pediococcus sp. which quantitatively converts it into 4-hydroxy-3-oxobutylphosphonate 4, an isosteric analog of dihydroxyacetone phosphate.Kinetic constants of the latter reaction were determined. - Keywords: Dihydroxyacetone phosphate mimic; Enzymatic synthesis; Glycerol phosphate oxidase; Sugar phosphonates
- Arth, Hans-Lothar,Sinerius, Gudrun,Fessner, Wolf-Dieter
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p. 2037 - 2042
(2007/10/03)
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