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Acetyllysine information


Acetyllysine
Skeletal formula of acetyllysine (S)
Names
Other names
  • 6-Acetamido-2-aminohexanoic acid[citation needed]
  • 2-Azaniumyl-6-acetamidohexanoate[citation needed]
Identifiers
CAS Number
  • 692-04-6 S checkY
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 Edit this at Wikidata
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 checkY
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).
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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 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.[1]

  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.

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Acetyllysine

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Acetyllysine (or acetylated lysine) is an acetyl-derivative of the amino acid lysine. There are multiple forms of acetyllysine: this article is about...

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Lysine

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dephosphorylated to the ε-aldehyde. The aldehyde is then transaminated to N‑acetyllysine, which is deacetylated to give L-lysine. However, the enzymes involved...

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Aceturic acid

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N-Acetylaspartic acid N-Acetylcysteine N-Acetylglutamic acid N-Acetylleucine Nε-Acetyllysine N-Acetyltyrosine Aceburic acid Haynes, William M., ed. (2016). CRC Handbook...

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Histone acetyltransferase

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proteins by transferring an acetyl group from acetyl-CoA to form ε-N-acetyllysine. DNA is wrapped around histones, and, by transferring an acetyl group...

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YEATS domain

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has an immunoglobulin like fold. The YEATS domain has shown to bind to acetyllysine protein modifications. In addition to lysine acetylation, the YEATS domain...

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Peptide library

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Residue 4: acetyllysine Residue 5: alanine Residue 6: isoleucine Residue 7: aspartic acid Residue 8: phenylalanine Residue 9: acetyllysine Residue 10:...

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C1orf112

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there are three polyadenylation signals. In addition, there is an N6-acetyllysine site at leucine 747 and a phosphoserine site at serine 23. C1orf112 has...

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Homocitrulline

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Rajantie J, Simell O, Perheentupa J: Oral administration of epsilon N-acetyllysine and homocitrulline in lysinuric protein intolerance. J Pediatr. 1983...

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TAF1

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transcription. TAF1 contains two bromodomains, which each can bind one of two acetyllysine residues at position 5 and 12 in the H4 tail, to stabilize the TBP-TATA...

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