Organocatalysis with endogenous compounds: Towards novel non-enzymatic reactions |
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| Authors: | David G Alberg Thomas B Poulsen Søren Bertelsen Kasper L Christensen Rune D Birkler Mogens Johannsen Karl Anker Jørgensen |
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| Institution: | 1. Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, DK, Denmark;2. Department of Chemistry, Carleton College, Northfield, MN 55057, USA;3. Department of Forensic Medicine, Section for Toxicology and Drug Analysis, Aarhus University, DK-8200 Aarhus N, DK, Denmark |
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| 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 reaction might take place in living organisms. |
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