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

In organisms, methylglyoxal is formed as a side-product of several 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 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.