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

Authors
Journal
Bioorganic & Medicinal Chemistry
0968-0896
Publisher
Elsevier
Publication Date
Volume
7
Issue
7
Identifiers
DOI: 10.1016/s0968-0896(99)00065-6
Keywords
  • Phosphonic Acids And Derivs
  • Isosteres
  • Substituent Effects
  • Enzymes And Enzyme Reactions
Disciplines
  • Biology

Abstract

Abstract The present paper describes the synthetic routes of six phosphono analogues of dihydroxyacetone phosphate and five phosphono analogues of glyceraldehyde 3-phosphate through α-, β- and γ-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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