Contents

Acetyllysine

Acetyllysine

Names
Other names 6-Acetamido-2-aminohexanoic acid[citation needed] 2-Azaniumyl-6-acetamidohexanoate[citation needed]
Identifiers
CAS Number	692-04-6 S Y
3D model (JSmol)	Interactive image
Beilstein Reference	1725438 S
ChEBI	CHEBI:17752 N
ChEMBL	ChEMBL1230958 N
ChemSpider	233732 N 83801 S N
ECHA InfoCard	100.010.661
EC Number	211-725-9
Gmelin Reference	747339 S
KEGG	C02727 N
MeSH	N-epsilon-acetyllysine
PubChem CID	265949 6994067 R 92832 S
UNII	470AD5VY1X S Y
CompTox Dashboard (EPA)	DTXSID90862371
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) N Key: DTERQYGMUDWYAZ-UHFFFAOYSA-N 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). N verify (what is YN ?) Infobox references

Chemical compound

Acetyllysine (or acetylated lysine) is an acetyl-derivative of the amino acid lysine. There are multiple forms of acetyllysine: this article is about N-ε-acetyl-L-lysine; the other form is N-α-acetyl-L-lysine.

Inproteins, the acetylation of lysine residues is an important mechanism of epigenetics. It functions by regulating the binding of histonestoDNAinnucleosomes 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]