Organocatalysis with endogenous compounds: Towards novel non-enzymatic reactions

…, TB Poulsen, S Bertelsen, KL Christensen…

Index: Alberg, David G.; Poulsen, Thomas B.; Bertelsen, Soren; Christensen, Kasper L.; Birkler, Rune D.; Johannsen, Mogens; Jorgensen, Karl Anker Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 14 p. 3888 - 3891

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Citation Number: 11

Abstract

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 ...