Synthesis of phosphono analogues of dihydroxyacetone phosphate and glyceraldehyde 3-phosphate

The present paper describes the synthetic routes of six phosphono analogues of dihydroxyacetone phosphate and five phosphono analogues of glyceraldehy de 3-phosphate through alpha-, beta- and gamma-hydroxyphosphonate esters pr ecursors containing a protected carbonyl group. In some situations, dependi ng on the sequence used for the deprotection of the phosphonate and carbony l groups, the aldol/ketol rearrangement allowed the synthesis of either dih ydroxyacetone phosphate or glyceraldehyde 3-phosphate analogues from the sa me precursors. All these analogues are of interest both as active-site prob es and as potential substrates for glycolytic enzymes such as fructose 1,6- diphosphate aldolases (EC 4.1.2.13). (C) 1999 Elsevier Science Ltd. All rig hts reserved.