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.
Alberg
David G
DG
Center for Catalysis, Department of Chemistry, Aarhus University, Aarhus C, Denmark.
Poulsen
Thomas B
TB
Bertelsen
Søren
S
Christensen
Kasper L
KL
Birkler
Rune D
RD
Johannsen
Mogens
M
Jørgensen
Karl Anker
KA
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