Liebigs Annalen

Enzymes in organic synthesis. Expedient enantioselective synthesis of (S)??(−)??3, 4??dihydroxybutylphosphonate, an isosteric substrate mimic for glycerol phosphate …

HL Arth, G Sinerius, WD Fessner

Index: Arth, Hans-Lothar; Sinerius, Gudrun; Fessner, Wolf-Dieter Liebigs Annalen, 1995 , # 11 p. 2037 - 2042

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Citation Number: 4

Abstract

Abstract The title compound (S)-(−)-2 was obtained in enantiomerically pure form and 47% 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- ...