N6-Acetyl-L-lysine

Common 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 particliar 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 regliate 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 histones basic N-terminal tail region. Within a histone octamer, these regions extend out from the associated globliar 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 regions positive charge, is postliated 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 intracellliar signaling mechanism that plays critical roles in regliating gene transcription, cell-cycle progression, apoptosis, DNA repair, and cytoskeletal organization. (PMID 9169194 , 10827952 , 17340003 , 16247734 , 9478947 , 10839822 ). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (2S)-6-(acetylamino)-2-Aminohexanoic acidChEBI N(6)-ACETYLLYSINEChEBI N(zeta)-AcetyllysineChEBI N-epsilon-Acetyl-L-lysineChEBI N-Epsilon-AcetyllysineChEBI N(epsilon)-Acetyl-L-lysineChEBI N(zeta)-Acetyl-L-lysineChEBI (2S)-6-(acetylamino)-2-AminohexanoateGenerator N(Z)-AcetyllysineGenerator N(ζ)-acetyllysineGenerator N(Z)-Acetyl-L-lysineGenerator N(ζ)-acetyl-L-lysineGenerator e-Acetyl-L-lysineHMDB e-N-Acetyl-L-lysineHMDB e-N-AcetyllysineHMDB epsilon-Acetyl-L-lysineHMDB epsilon-N-Acetyl-L-lysineHMDB epsilon-N-AcetyllysineHMDB L-e-N-AcetyllysineHMDB L-epsilon-N-AcetyllysineHMDB N-e-Acetyl-L-lysineHMDB N-e-AcetyllysineHMDB N6-AcetyllysineHMDB Ne-acetyl-L-lysineHMDB Ne-acetyllysineHMDB Omega-N-acetyl-L-lysineHMDB W-N-Acetyl-L-lysineHMDB N(6)-AcetyllsineMeSH Omega-acetyllsineMeSH

Chemical Formlia

C₈H₁₆N₂O₃ Average Molecliar Weight

188.2242 Monoisotopic Molecliar Weight

188.116092388 IUPAC Name

(2S)-2-amino-6-acetamidohexanoic acid Traditional Name

N6-acetyllysine CAS Registry Number

692-04-6 SMILES

CC(=O)NCCCC[C@H](N)C(O)=O

InChI Identifier

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 Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

L-alpha-amino acids Alternative Parents

Medium-chain fatty acids

Amino fatty acids

Amino acids

Propargyl-type 1,3-dipolar organic compounds

Monocarboxylic acids and derivatives

Carboxylic acids

Carboximidic acids

Organopnictogen compounds

Organic oxides

Monoalkylamines

Hydrocarbon derivatives

Carbonyl compounds

Substituents

L-alpha-amino acid

Medium-chain fatty acid

Amino fatty acid

Fatty acid

Fatty acyl

Amino acid

Carboximidic acid

Carboximidic acid derivative

Carboxylic acid

Monocarboxylic acid or derivatives

Propargyl-type 1,3-dipolar organic compound

Organic 1,3-dipolar compound

Primary amine

Organooxygen compound

Organonitrogen compound

Carbonyl group

Primary aliphatic amine

Organic nitrogen compound

Organic oxygen compound

Amine

Organopnictogen compound

Organic oxide

Hydrocarbon derivative

Aliphatic acyclic compound

Molecliar Framework

Aliphatic acyclic compounds External Descriptors

N(6)-acyl-L-lysine (CHEBI:17752 )

acetyl-L-lysine (CHEBI:17752 )

Ontology Status

Detected and Quantified Origin

Endogenous

Biofunction

Protein synthesis, amino acid biosynthesis

Application

Not Available Cellliar locations

Cytoplasm (predicted from logP)

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point250 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility17.5 mg/mLALOGPS logP-2.6ALOGPS logP-3.2ChemAxon logS-1ALOGPS pKa (Strongest Acidic)2.43ChemAxon pKa (Strongest Basic)9.53ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 Å²ChemAxon Rotatable Bond Count6ChemAxon Refractivity47.25 m³·mol^-1ChemAxon Polarizability20.28 Å³ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key GC-MS

GC-MS Spectrum – GC-MS (3 TMS)splash10-0002-9610000000-6e30cfdb2a70cc49f983View in MoNA GC-MS

GC-MS Spectrum – GC-EI-TOFsplash10-004i-1900000000-e36d5532f4f0ed8ec34fView in MoNA GC-MS

GC-MS Spectrum – GC-EI-TOFsplash10-0002-9500000000-266c8b0fce84c71553b2View in MoNA GC-MS

GC-MS Spectrum – GC-EI-TOFsplash10-0002-9500000000-266c8b0fce84c71553b2View in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-004r-1900000000-4745f7cfa9eaaef208adView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-635805826359aa05ec7cView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-8857489c6ac957c71a5dView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-39f91157038523017046View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000j-0900000000-183e1f50c20603f14c03View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-1900000000-da02d0f8bd73b5b96b46View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4j-9400000000-8531cdbb4e8108dbec95View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9000000000-94d72f2c644db8c0b5cdView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0900000000-c6ff005564503774a853View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004i-3900000000-dffc604f608a010e711eView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-d6bc330de42890c4c091View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-8d68337bf7a8db380cd7View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-1400569a447d5f66c3a8View in MoNA 1D NMR

1H NMR SpectrumNot Available 2D NMR

[1H,13C] 2D NMR SpectrumNot Available

Biological Properties Cellliar Locations

Cytoplasm (predicted from logP)

Biofluid Locations

Blood

Saliva

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot Available

Normal