Chemistry:Acetyllysine

Acetyllysine

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

|Section1=! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

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CAS Number

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• 692-04-6 S ^Y

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3D model (JSmol)

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• Interactive image

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Beilstein Reference

| 1725438 S |- | ChEBI

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• CHEBI:17752 ^N

|- | ChEMBL

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• ChEMBL1230958 ^N

|- | ChemSpider

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• 233732 ^N
• 83801 S ^N

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| EC Number

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• 211-725-9

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Gmelin Reference

| 747339 S |-

| KEGG

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• C02727 ^N

|- | MeSH | N-epsilon-acetyllysine |-

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PubChem CID

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• 265949
• 6994067 R
• 92832 S

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| UNII

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• 470AD5VY1X S ^Y

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| colspan="2" |

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

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| colspan="2" |

SMILES

• CC(=O)NCCCC[C@H](N)C(=O)O

|- |Section2=! colspan=2 style="background: #f8eaba; text-align: center;" |Properties

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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)

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| log P | −0.961 |-

| Acidity (pK_a) | 2.529 |- | Basicity (pK_b) | 11.468 |- |Section3=! colspan=2 style="background: #f8eaba; text-align: center;" |Related compounds

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Related alkanoic acids

| Pivagabine |- }}

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.

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.