Organocatalysis with endogenous compounds: towards novel non-enzymatic reactions.

  title={Organocatalysis with endogenous compounds: towards novel non-enzymatic reactions.},
  author={David G. Alberg and Thomas B Poulsen and S{\o}ren Bertelsen and Kasper L. Christensen and Rune Isak Dupont Birkler and Mogens Johannsen and Karl Anker J{\o}rgensen},
  journal={Bioorganic & medicinal chemistry letters},
  volume={19 14},
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.