2009•SynfactsRequires access
Enzymatic Control over Self- and Cross-Aldol Reactions
Xavier Garrabou, José Antonio García del Castillo, Christine Guérard‐Hélaine, Teodor Parella, Jesús Joglar, Marielle Lemaire, Pere Clapés
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Abstract
Significance The enzyme-catalyzed self- and cross-aldol additions of glycolaldehyde (GA) are reported. The investigated enzyme d -fructose-6-phosphate aldolase (FSA) proved to be very effective and able to differentiate carbonyl compounds in its donor and acceptor capabilities. Glycolaldehyde showed the highest donor properties, as illustrated in kinetic studies by its low Michaelis-Menten constant. The K M of glycolaldehyde was even lower than those for dihydroxyacetone and hydroxyacetone, respectively, both known to be well tolerated as donors by the FSA enzyme. Remarkably, even consecutive aldol additions were possible.