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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
Author(s) -
SánchezMoreno Israel,
Hélaine Virgil,
Poupard Nicolas,
Charmantray Franck,
Légeret Bertrand,
Hecquet Laurence,
GarcíaJunceda Eduardo,
Wohlgemuth Roland,
GuérardHélaine Christine,
Lemaire Marielle
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200150
Subject(s) - aldolase a , glycolaldehyde , aldolase b , dihydroxyacetone phosphate , chemistry , fructose , aldol reaction , fructose bisphosphate aldolase , phosphate , glyceraldehyde , arabinose , organic chemistry , biochemistry , enzyme , fermentation , catalysis , xylose , dehydrogenase
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.