Acetyllysine

Acetyllysine

Names
Other names 6-Acetamido-2-aminohexanoic acid 2-Azaniumyl-6-acetamidohexanoate
Identifiers
CAS Number	692-04-6 S
3DMet	B01598
Beilstein Reference	1725438 S
ChEBI	CHEBI:17752
ChEMBL	ChEMBL1230958
ChemSpider	233732 83801 S
EC Number	211-725-9
Gmelin Reference	747339 S
Jmol interactive 3D	Image Image
KEGG	C02727
MeSH	N-epsilon-acetyllysine
PubChem	265949 6994067 R 92832 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]):[nH]CCCCC(N)c(:[o]):[oH] CC(=O)NCCCCC(N)C(O)=O
Properties
Chemical formula	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

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.