Bioorganic and Medicinal Chemistry Letters
Organocatalysis, Aldol, Non-enzymatic, Acetone, Methylglyoxal
The aldol reaction of the endogeneous compounds acetone and methylglyoxal has been studied using organocatalysis in relation to biologically relevant non-enzymatic reactions. Under preparative conditions, 3-hydroxy-2,5-hexadione, known as Henze’s ketol, is formed in high yield and with enantioselectivities up to 88% ee. Furthermore, Henze’s ketol is also formed under simulated physiological conditions at micromolar scale, indicating that this reaction might take place in living organisms.
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Alberg, David G., Thomas B. Poulsen, Søren Bertelsen, Kasper L. Christensen, Rune D. Birkler, Mogens Johannsen, and Karl A. Jørgensen., "Organocatalysis with Endogenous Compounds: Towards Novel Non-enzymatic Reactions". Bioorganic and Medicinal Chemistry Letters. 2009, 19: 3888-3891. Available at: https://doi.org/10.1016/j.bmcl.2009.03.128. Accessed via Faculty Work. Chemistry. Carleton Digital Commons. https://digitalcommons.carleton.edu/chem_faculty/10
The definitive version is available at https://doi.org/10.1016/j.bmcl.2009.03.128