methylglyoxal
| Methylglyoxal | |
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| IUPAC name | 2-oxopropanal |
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| 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 |
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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. In the body, methylglyoxal may form from 3-amino acetone, which is an intermediate of threonine catabolism. Also lipid oxidation is a source for methylglyoxal. 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 glutathion forming a hemithioacetal. This is converted into S-D-Lactoyl-Glutathione by glyoxalaseI, and then further metabolised into D-lactate by glyoxalaseII. Why methylglyoxal is produced remains unknown, but several articles point to the fact 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). 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:
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