Stereospecific deuteration of 2-deoxyerythrose 4-phosphate using 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase

Racemic 2-deoxyerythrose 4-phosphate was synthesized and one enantiomer of this compound was found to be a substrate for Escherichia coli 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase, the first enzyme of the shikimate pathway. When the reaction was carried out in deuterium oxide, an enzyme-catalyzed regio- and stereoselective incorporation of deuterium into the product was observed.

Graphical abstractThe synthesis of racemic 2-deoxyerythrose 4-phosphate and the selection of one enantiomer of this compound as a substrate for 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase are reported. When the enzyme reaction was carried out in deuterium oxide stereospecific deuteration of the product was observed.Figure optionsDownload full-size imageDownload as PowerPoint slide