2012Advanced Synthesis & CatalysisRequires access

One‐Pot Cascade Reactions using Fructose‐6‐phosphate Aldolase: Efficient Synthesis of D ‐Arabinose 5‐Phosphate, D ‐Fructose 6‐Phosphate and Analogues

Israel Sánchez‐Moreno, Virgil Hélaine, Nicolas Poupard, Franck Charmantray, Bertrand Légeret, Laurence Hecquet, Eduardo García‐Junceda, Roland Wohlgemuth, Christine Guérard‐Hélaine, Marielle Lemaire

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Abstract

Abstract One‐pot multienzymatic reactions have been performed for the synthesis of 1‐deoxy‐D‐fructose 6‐phosphate, 1,2‐dideoxy‐D‐arabino‐hept‐3‐ulose 7‐phosphate, D‐fructose 6‐phosphate and D‐arabinose 5‐phosphate. The whole synthetic strategy is based on an aldol addition reaction catalysed by fructose‐6‐phosphate aldolase (FSA) as a key step of a three or four enzymes‐catalysed cascade reaction. The four known donors for FSA – dihydroxyacetone (DHA), hydroxyacetone (HA), 1‐hydroxy‐2‐butanone (HB) and glycolaldehyde (GA) – were used with D‐glyceraldehyde 3‐phosphate as acceptor substrate. The target phosphorylated sugars were obtained in good to excellent yields and high purity.

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Abstract One‐pot multienzymatic reactions have been performed for the synthesis of 1‐deoxy‐D‐fructose 6‐phosphate, 1,2‐dideoxy‐D‐arabino‐hept‐3‐ulose 7‐phosphate, D‐fructose 6‐phosphate and D‐arabinose 5‐phosphate. The whole synthetic strategy is based on an aldol addition reaction catalysed by fructose‐6‐phosphate aldolase (FSA) as a key step of a three or four enzymes‐catalysed cascade reaction. The four known donors for FSA – dihydroxyacetone (DHA), hydroxyacetone (HA), 1‐hydroxy‐2‐butanone (HB) and glycolaldehyde (GA) – were used with D‐glyceraldehyde 3‐phosphate as acceptor substrate. The target phosphorylated sugars were obtained in good to excellent yields and high purity.

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Available abstract

Abstract One‐pot multienzymatic reactions have been performed for the synthesis of 1‐deoxy‐D‐fructose 6‐phosphate, 1,2‐dideoxy‐D‐arabino‐hept‐3‐ulose 7‐phosphate, D‐fructose 6‐phosphate and D‐arabinose 5‐phosphate. The whole synthetic strategy is based on an aldol addition reaction catalysed by fructose‐6‐phosphate aldolase (FSA) as a key step of a three or four enzymes‐catalysed cascade reaction. The four known donors for FSA – dihydroxyacetone (DHA), hydroxyacetone (HA), 1‐hydroxy‐2‐butanone (HB) and glycolaldehyde (GA) – were used with D‐glyceraldehyde 3‐phosphate as acceptor substrate. The target phosphorylated sugars were obtained in good to excellent yields and high purity.

Key concepts: Aldolase A, Glycolaldehyde, Aldolase B, Dihydroxyacetone phosphate, Chemistry, Fructose, Aldol reaction, Fructose-bisphosphate aldolase

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One‐Pot Cascade Reactions using Fructose‐6‐phosphate Aldolase: Efficient Synthesis of D ‐Arabinose 5‐Phosphate, D ‐Fructose 6‐Phosphate and Analogues — Research Paper | ScholarLens