Methylglyoxal, also called
pyruvaldehyde or
2-oxo-propanal (CH3-CO-CH=O or C3H4O2) is the
aldehyde form of
pyruvic acid. It has two
carbonyl groups, so it is a
dicarbonyl compound. Methylglyoxal is both an aldehyde and a
ketone. In the body, methylglyoxal may form from 3-amino
acetone, which is an intermediate of
threonine catabolism. This compound, as well as
glyoxal, is a byproduct of metabolism, but cannot be used. The aldehyde reacts with
glutathione, a
tripeptide consisting of
glutamic acid,
cysteine, and
glycine. Glutathione reduces methylglyoxal to
1-hydroxy acetone, a ketol. 1-Hydroxy acetone goes through
enediol tautomerism to lactaldehyde. Then the lactaldehyde is oxidised by glutathione to D-
lactic acid. Methylglyoxal is also called a
ketal, because it has an aldehydic and ketonic carbonyl group. It is a type of the
advanced glycation endproducts(AGEs) resulting from sugar modifications, such as the
Maillard reaction. When the
reductone is cleaved, pyruvaldehyde forms. There are 4 main
glycation sugars:
External links
Aldehydes | Ketones | Metabolism
"Methylglyoxal"