My watch list
my.chemeurope.com  
Login  

Methylglyoxal



Methylglyoxal
IUPAC name 2-oxopropanal
Identifiers
CAS number 78-98-8
PubChem 880
MeSH Methylglyoxal
SMILES CC(=O)C=O
Properties
Molecular formula C3H4O2
Molar mass 72.0627
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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. Methylglyoxal is also called a ketal, because it has an aldehydic and ketonic carbonyl group.

Additional recommended knowledge

In organisms, methylglyoxal is formed as a side-product of several metabolic pathways.[1] It may form from 3-amino acetone, which is an intermediate of threonine catabolism, as well as through lipid peroxidation. However, the most important source is glycolysis. Here, methylglyoxal arises from non enzymatic phosphate elimination from glyceraldehyde phosphate en dihydroxyacetone phosphate, two intermediates of glycolysis. Since methylglyoxal is highly cytotoxic the body developed several detoxification mechanisms. One of these is the glyoxalase system. Methylglyoxal reacts with glutathione forming a hemithioacetal. This is converted into S-D-Lactoyl-Glutathione by glyoxalase I,[2] and then further metabolised into D-lactate by glyoxalase II.[3]

Why methylglyoxal is produced remains unknown, but several articles indicate that methylglyoxal is involved in the formation of advanced glycation endproducts (AGEs). In fact, methylglyoxal is proven to be the most important glycation agent (forming AGEs) [4]. In this process, methylglyoxal reacts with free amino groups of lysine and arginine residues of proteins forming AGEs. Other glycation agents include reducing sugars like:

References

  1. ^ Inoue Y, Kimura A (1995). "Methylglyoxal and regulation of its metabolism in microorganisms". Adv. Microb. Physiol. 37: 177–227. PMID 8540421.
  2. ^ Thornalley PJ (2003). "Glyoxalase I--structure, function and a critical role in the enzymatic defence against glycation". Biochem. Soc. Trans. 31 (Pt 6): 1343–8. PMID 14641060.
  3. ^ Vander Jagt DL (1993). "Glyoxalase II: molecular characteristics, kinetics and mechanism". Biochem. Soc. Trans. 21 (2): 522–7. PMID 8359524.
  4. ^ Shinohara M (1998). "Overexpression of glyoxalase-I in bovine endothelial cells inhibits intracellular advanced glycation endproduct formation and prevents hyperglycemia-induced increases in macromolecular endocytosis.". J Clin Invest. 101 (5): 1142–7. PMID 9486985.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Methylglyoxal". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE