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 glyceraldehyde 3-phosphate through alpha-, beta- and gamma-hydroxyphosphonate esters precursors containing a protected carbonyl group. In some situations, depending on the sequence used for the deprotection of the phosphonate and carbonyl groups, the aldol/ketol rearrangement allowed the synthesis of either dihydroxyacetone phosphate or glyceraldehyde 3-phosphate analogues from the same precursors. All these analogues are of interest both as active-site probes and as potential substrates for glycolytic enzymes such as fructose 1,6-diphosphate aldolases (EC 4.1.2.13).
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Groupe de Chimie Organique Biologique, UMR 5623, Université Paul Sabatier, Toulouse, France.
Blonski
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Périé
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D000818:Animals; D004099:Dihydroxyacetone Phosphate / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism; D005634:Fructose-Bisphosphate Aldolase / Q000378:metabolism; D005986:Glyceraldehyde 3-Phosphate / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism; D018482:Muscle, Skeletal / Q000201:enzymology; D063065:Organophosphonates / Q000737:chemistry; D011817:Rabbits; D013379:Substrate Specificity
D063065:Organophosphonates; D005986:Glyceraldehyde 3-Phosphate; D004099:Dihydroxyacetone Phosphate; D005634:Fructose-Bisphosphate Aldolase