Acetyllysine
 | |
| Names | |
|---|---|
Other names
| |
| Identifiers | |
692-04-6 S  | |
| 3D model (Jmol) | Interactive image Interactive image |
| 3DMet | B01598 |
| 1725438 S | |
| ChEBI | CHEBI:17752 |
| ChEMBL | ChEMBL1230958 |
| ChemSpider | 233732 83801 S |
| ECHA InfoCard | 100.010.661 |
| EC Number | 211-725-9 |
| 747339 S | |
| KEGG | C02727 |
| MeSH | N-epsilon-acetyllysine |
| PubChem | 265949 6994067 R 92832 S |
| |
| |
| Properties | |
| C8H16N2O3 | |
| Molar mass | 188.23 g·mol−1 |
| Appearance | White crystals |
| Odor | Odourless |
| Density | 1.139 g/mL |
| Melting point | 250 °C (482 °F; 523 K) |
| Boiling point | 442 °C (828 °F; 715 K) |
| log P | −0.961 |
| Acidity (pKa) | 2.529 |
| Basicity (pKb) | 11.468 |
| Related compounds | |
| Related alkanoic acids |
Pivagabine |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is  ?) | |
| Infobox references | |
Acetyllysine (or acetylated lysine) is an acetyl-derivative of the amino acid lysine. There are multiple forms of acetyllysine - this article refers to N-ε-acetyl-L-lysine. The other form is N-α-acetyl-L-lysine.
In proteins, the acetylation of lysine residues is an important mechanism of epigenetics. It functions by regulating the binding of histones to DNA in nucleosomes and thereby controlling the expression of genes on that DNA. Non-histone proteins are acetylated as well. Unlike the functionally similar methyllysine, acetyllysine does not carry a positive charge on its side chain.
Histone acetyltransferases (HATs) catalyze the addition of acetyl groups from acetyl-CoA onto certain lysine residues of histones and non-histone proteins. Histone deacetylases (HDACs) catalyze the removal of acetyl groups from acetylated lysines.
Acetyllysine can be synthesized from lysine by the selective acetylation of the terminal amine group.[1]
References
- ↑ For example: Kikugawa, Mitsui, Sakamoto (1990). "N-methoxydiacetamide: A new selective acetylating agent". Journal Tetrahedron Letters. 31 (2): 243–246. doi:10.1016/S0040-4039(00)94382-X.