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Asymmetric Self- and Cross-Aldol Reactions of Glycolaldehyde Catalyzed by D-Fructose-6-phosphate Aldolase

Authors

  • Xavier Garrabou,

    1. Biotransformation and Bioactive Molecules Group, Instituto de Química Avanzada de Cataluña-CSIC, Jordi Girona 18-26, 08034 Barcelona (Spain), Fax: (+34) 93-204-5904
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  • José A. Castillo Dr.,

    1. Université Blaise Pascal, Laboratoire SEESIB-CNRS, UMR 6504-Synthèse et Etude de Systèmes à Intérêt Biologique, 24 avenue des Landais, 63177 Aubière, Aubière Cedex (France)
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  • Christine Guérard-Hélaine Dr.,

    1. Université Blaise Pascal, Laboratoire SEESIB-CNRS, UMR 6504-Synthèse et Etude de Systèmes à Intérêt Biologique, 24 avenue des Landais, 63177 Aubière, Aubière Cedex (France)
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  • Teodor Parella Dr.,

    1. Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, Bellaterra (Spain)
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  • Jesús Joglar Dr.,

    1. Biotransformation and Bioactive Molecules Group, Instituto de Química Avanzada de Cataluña-CSIC, Jordi Girona 18-26, 08034 Barcelona (Spain), Fax: (+34) 93-204-5904
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  • Marielle Lemaire Prof.,

    1. Université Blaise Pascal, Laboratoire SEESIB-CNRS, UMR 6504-Synthèse et Etude de Systèmes à Intérêt Biologique, 24 avenue des Landais, 63177 Aubière, Aubière Cedex (France)
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  • Pere Clapés Dr.

    1. Biotransformation and Bioactive Molecules Group, Instituto de Química Avanzada de Cataluña-CSIC, Jordi Girona 18-26, 08034 Barcelona (Spain), Fax: (+34) 93-204-5904
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  • This work was supported by the Spanish MCINN (CTQ2006-01345/BQU, CTQ2006-01080), La Marató de TV3 foundation (Ref: 050931), Generalitat de Catalunya (DURSI 2005-SGR-00698), and ESF (project COST CM0701). X.G. acknowledges the I3P-CSIC predoctoral scholarship program. J.A.C. acknowledges the French foundation Vaincre Les Maladies Lysosomales for a postdoctoral fellowship. We thank Prof. Wolf-Dieter Fessner, Prof. Georg A. Sprenger, and Dr. Thierry Gefflaut for their helpful advice and fruitful discussions.

Abstract

original image

New facets of enzyme activity: D-Fructose-6-phosphate aldolase (FSA) catalyzes the self-aldol reaction of glycolaldehyde (GA) and its cross-aldol addition to other aldehydes. As the affinity of GA for FSA as a donor is higher than that as an acceptor, cross-aldol reactions are possible with good to poor aldehyde acceptors if the concentration of GA in the reaction is kept low.

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