✦ LIBER ✦
Enzymes in organic synthesis. Expedient enantioselective synthesis of (S)-(−)-3,4-dihydroxybutylphosphonate, an isosteric substrate mimic for glycerol phosphate oxidase
✍ Scribed by Arth, Hans-Lothar ;Sinerius, Gudrun ;Fessner, Wolf-Dieter
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 718 KB
- Volume
- 1995
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
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‐oxobutylphosphonate 4, an isosteric analog of dihydroxyacetone phosphate. Kinetic constants of the latter reaction were determined.