Monofluorophosphonates as phosphate mimics in bioorganic chemistry: a comparative study of CH2-, CHF- and CF2-phosphonate analogues of sn-glycerol-3-phosphate as substrates for sn-glycerol-3-phosphate dehydrogenase

Abstract

The synthesis of the cyclohexylammonium salts of 3-(S),4-dihydroxy-1(R,S)-fluorobutylphosphonic acid 3 and 1,1-difluoro-3-(S),4-dihydroxybutylphosphonic acid 4 is reported; 3 is a better substrate for NADH linked sn-glycerol-3-phosphate dehydrogenase than the difluoromethylenephosphonate 4; a comparative study of the CH₂-, CHF and CF₂- phosphonate analogues of sn-glycerol-3-phosphate is reported.