Basic information
- CAS
692-04-6- Standard SMILES
CC(=O)NCCCC[C@H]([NH3+])C(=O)[O-]- InChIKey
DTERQYGMUDWYAZ-ZETCQYMHSA-N- Molecular formula
- C8H16N2O3
- Average molar mass
- 188.22 g/mol
- Monoisotopic mass
- 188.11609238
Overview
N(6)-acetyl-L-lysine zwitterion is an amino acid zwitterion obtained via transfer of a proton from the carboxy to the amino group of N6-acetyl-L-lysine; major species at pH 7.3. It is a tautomer of a N(6)-acetyl-L-lysine.
Names & identifiers
- Preferred name
- Acetyllysine
- IUPAC
- (2S)-6-acetamido-2-azaniumylhexanoate
- English name
- N-epsilon-Acetyl-L-lysine
- Molecular formula
- C8H16N2O3
- Molecular weight
- 188.22
Names & synonyms
acetyllysineS-6-acetamido-2-aminohexanoic acidCHEBI:58260N(6)-acetyl-L-lysine zwitterion(2S)-6-acetamido-2-ammoniohexanoate(2S)-6-acetamido-2-azaniumylhexanoateH-LYS(AC)-OHN6-Acetyllysinelys(ac)N-epsilon-acetyllysineN-EPSILON-ACETYL-L-LYSNSC 102777
Show more names
LYSINE(AC)-OHH-L-LYS(AC)-OHNε-Ac-L-Lys-OHNε-Acetyllysine
Database identifiers
- CAS
692-04-6- PubChem CID
- 6991978
- ChEBI
CHEBI:58260
Properties
Computed structural properties
- XLogP
- -2.3
- Topological polar surface area
- 96.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 177
Experimental & physicochemical properties
Melting Point250 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 250 °C · 250 °C (dec.)(lit.)
- Boiling point
- 323.23 °C · 323.23°C (rough estimate)
- Density
- 1.1793 · 1.1793 (rough estimate)
- refractive index
- 1.45 · 1.4500 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Aqueous Base (Slightly), Water (Slightly)
- form
- Powder
- pka
- 2.53 · 2.53±0.24(Predicted)
- color
- White
- Water Solubility
- 80 % · Soluble in water (miscible), and 80% acetic acid (50 mg/ml).
- Sensitive
- Hygroscopic
- InChI
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- hs_code
- 29241900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P280-P261
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Applications
DescriptionAcetyllysine (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-Llysine. 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.
UsesN-Epsilon-acetyl-l-lysine is used in the metabolomics study on the combined effect of cocaine and ethanol via liquid chromatography-mass spectrometry metabolomics approach.
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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