Acetyllysine

Acetyllysine
Names
	Other names 6-Acetamido-2-aminohexanoic acid; 2-Azaniumyl-6-acetamidohexanoate;
Identifiers
CAS Number	692-04-6 S ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1725438 S
ChEBI	CHEBI:17752 ;
ChEMBL	ChEMBL1230958 ;
ChemSpider	233732 ; 83801 S ;
ECHA InfoCard	100.010.661
EC Number	211-725-9;
Gmelin Reference	747339 S
KEGG	C02727 ;
MeSH	N-epsilon-acetyllysine
PubChem CID	265949; 6994067 R; 92832 S;
UNII	470AD5VY1X S ;
	InChI InChI=1S/C8H16N2O3/c1-6(11)10-5-3-2-4-7(9)8(12)13/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13) Key: DTERQYGMUDWYAZ-UHFFFAOYSA-N ;
	SMILES CC(=O)NCCCC[C@H](N)C(=O)O;
Properties
Chemical formula	C8H16N2O3
Molar mass	188.227 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).
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	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.

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[1] 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.