| Methylglyoxal | |
|---|---|
 |
|
| IUPAC name |
2-oxopropanal
|
| Identifiers | |
| CAS number | 78-98-8  |
| PubChem | 880 |
| MeSH | Methylglyoxal |
| SMILES |
CC(=O)C=O
|
| ChemSpider ID | 857 |
| Properties | |
| Molecular formula | C3H4O2 |
| Molar mass | 72.0627 |
| Related compounds | |
| Related ketones, aldehydes | glyoxal propionaldehyde propanedial acetone diacetyl acetylacetone |
| Related compounds | glyoxylic acid pyruvic acid acetoacetic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox 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.
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 and with thiol groups of cysteine forming AGEs. Other glycation agents include reducing sugars like
- glucose, the sugar that stores energy,
- galactose, a part of milk sugar (lactose),
- allose, an all-cis hexose carried into the cell by special proteins, and
- ribose, a component of RNA.
References
- ^ Inoue Y, Kimura A (1995). "Methylglyoxal and regulation of its metabolism in microorganisms". Adv. Microb. Physiol. 37: 177–227 year=1995. doi:. PMID 8540421.
- ^ 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. doi:. PMID 14641060. http://www.biochemsoctrans.org/bst/031/1343/bst0311343.htm.
- ^ Vander Jagt DL (1993). "Glyoxalase II: molecular characteristics, kinetics and mechanism". Biochem. Soc. Trans. 21 (2): 522–7. PMID 8359524.
- ^ 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. doi:. PMID 9486985.
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