Organocatalysis with endogenous compounds: towards novel non-enzymatic reactions.
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.
Center for Catalysis, Department of Chemistry, Aarhus University, Aarhus C, Denmark.
David G
DG
Alberg
Thomas B
TB
Poulsen
Søren
S
Bertelsen
Kasper L
KL
Christensen
Rune D
RD
Birkler
Mogens
M
Johannsen
Karl Anker
KA
Jørgensen
D000090:Acetoacetates / Q000737:chemistry; D000096:Acetone / Q000737:chemistry*; D002384:Catalysis; D006588:Hexanones / Q000138:chemical synthesis* / Q000737:chemistry; D011765:Pyruvaldehyde / Q000737:chemistry*
C544467:3-hydroxy-2,5-hexadione; D000090:Acetoacetates; D006588:Hexanones; D000096:Acetone; C016635:acetoacetic acid; D011765:Pyruvaldehyde