N6-acetyl-L-lysine

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  • Name: N6-acetyl-L-lysine
  • Description: N-acetyl-lysine is an acetylated amino acid. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins. Acetylation of specific lysine residues ... in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. By modifying chromatin proteins and transcription-related factors, these acetylases are believed to regulate the transcription of many genes. The best-characterized mechanism is acetylation, catalyzed by histone acetyltransferase (HAT) enzymes. HATs function enzymatically by transferring an acetyl group from acetyl-coenzyme A (acetyl-CoA) to the -amino group of certain lysine side chains within a histone's basic N-terminal tail region. Within a histone octamer, these regions extend out from the associated globular domains, and in the context of a nucleosome, they are believed to bind the DNA through charge interactions (positively charged histone tails associated with negatively charged DNA) or mediate interactions between nucleosomes. Lysine acetylation, which neutralizes part of a tail region's positive charge, is postulated to weaken histone-DNA or nucleosome-nucleosome interactions and/or signal a conformational change, thereby destabilizing nucleosome structure or arrangement and giving other nuclear factors, such as the transcription complex, more access to a genetic locus. In agreement with this is the fact that acetylated chromatin has long been associated with states of transcriptional activation. Specific recognition of N-acetyl-lysine is a conserved function of all bromodomains found in different proteins, recognized as an emerging intracellular signaling mechanism that plays critical roles in regulating gene transcription, cell-cycle progression, apoptosis, DNA repair, and cytoskeletal organization. (PMID 9169194,10827952,17340003, 1624773, 9478947, 10839822 ). This compound has shown higher levels in the blood of elderly healthy people, as compared to young healthy people, especially in correlation with other compounds. (HMDB:HMDB0000206, PNAS April 19, 2016 113 (16) 4252-4259)
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
27036001 Age [25-33], Gender ⚥ 0.38 (CV (CV=SD of metabolite abundance (peak areas from LC-MS) divided by the mean)) LC-MS red blood cells, plasma, blood
27036001 Age [74-88], Gender ⚥ 0.38 (CV (CV=SD of metabolite abundance (peak areas from LC-MS) divided by the mean)) LC-MS red blood cells, plasma, blood
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    ε-N-acetyl-L-lysine; N-ε-acetyllysine;N6-acetyl-lysine; acetyllysine
  • Chemical Formula:
    C8H16N2O3
  • Systematic name:
    (2S)-6-acetamido-2-aminohexanoic acid
  • SMILES:
    CC(=O)NCCCCC(C(=O)O)N
  • 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)/t7-/m0/s1
  • InChI Key:
    DTERQYGMUDWYAZ-ZETCQYMHSA-N
  • CAS number:
    692-04-6
Related resources
Pathway info P = product of S = substrate of
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Human body biofluids, Biofluid tissues, Blood, Saliva, Urine, Tissue, Cellular (general class), Subcellular, Cytoplasm, Excreta material, Feces
  • Metabolite source:
    Homo sapiens, exogenous metabolite
Age-variations
Age group comparisons
Method: LC-MS
Sample: red blood cells; plasma; blood
PubMed PMID: 27036001