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• W2124607285 abstract "The synthesis of the cyclohexylammonium salts of (1RS, 3S)-3,4-dihydroxy-1-fluorobutylphosphonic acid 3 and (S)-difluoro-3,4-dihydroxybutylphosphonic acid 4 is reported. These compounds are fluorinated phosphonate analogues of sn-glycerol-3-phosphate where the bridging phosphate ester oxygen is replaced by CHF and CF2 respectively. Kinetic studies are presented for oxidation with NADH linked glycerol-3-phosphate dehydrogenase, which reveal that the CHF-phosphonate 3 performs similarly to the natural substrate sn-glycerol-3-phosphate, and is a better substrate than the CF2-phosphonate 4. The study also reveals that the diastereoisomers of 3 (3a and 3b) are processed at different rates suggesting that the enzyme can discriminate the CHF stereogenic centres. A synthesis and X-ray crystal structure of 2-amino-1-fluoroethylphosphonic acid 7 is described which allows comparison of the geometry and conformation of CHF-phosphonate with that of analogous CH2- and CF2-phosphonates." @default.
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• W2124607285 date "1996-01-01" @default.
• W2124607285 modified "2023-10-07" @default.
• W2124607285 title "Synthesis of monofluoro- and difluoro- methylenephosphonate analogues of sn-glycerol-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moiety" @default.
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• W2124607285 doi "https://doi.org/10.1016/0040-4020(95)00890-k" @default.
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