| Revision as of 19:59, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 460110129 of page Acetyllysine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'ChEBI', 'KEGG', 'StdInChI', 'StdInChIKey', 'CASNo'). |
Latest revision as of 11:55, 22 December 2023 edit Teaktl17 (talk | contribs)Extended confirmed users17,957 edits + Category:Amino acid derivatives |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 457802348 |
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| verifiedrevid = 477240522 |
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| Reference = <ref> at ]</ref> |
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| ImageFile = Acetyllysine.svg |
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| ImageFile = Acetyllysine.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageName = Skeletal formula of acetyllysine (S) |
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| ImageSize = 244 |
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| OtherNames = {{Unbulleted list|6-Acetamido-2-aminohexanoic acid{{Citation needed|date=May 2012}}|2-Azaniumyl-6-acetamidohexanoate{{Citation needed|date=May 2012}} |
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| ImageName = Skeletal formula of acetyllysine |
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| PIN = 6-Acetamido-2-aminohexanoic acid{{Citation needed|date = July 2011}} |
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| SystematicName = 2-Azaniumyl-6-acetamidohexanoate{{Citation needed|date = July 2011}} |
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| OtherNames = 6-''N''-Acetyllysine{{Citation needed|date = July 2011}}<br /> |
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N<sub>ε</sub>-Acetyllysine{{Citation needed|date = July 2011}}<br /> |
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2-Aminio-6-acetamidohexanoate{{Citation needed|date = July 2011}} |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 692-04-6 --> |
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| CASNo_Comment = <small>(2''S'')-2-amino</small> |
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| PubChem2 = 265949 |
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| PubChem2_Ref = {{Pubchemcite|correct|pubchem}} |
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| PubChem1 = 6994067 |
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| PubChem1_Ref = {{pubchemcite|correct|pubchem}} |
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| PubChem1_Comment = <small>(2''R'')-2-amino</small> |
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| PubChem = 92832 |
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| PubChem_Ref = {{pubchemcite|correct|pubchem}} |
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| PubChem_Comment = <small>(2''S'')-2-amino</small> |
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| ChemSpiderID2 = 233732 |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 5362106 |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Comment = <small>(2''R'')-2-amino</small> |
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| ChemSpiderID = 83801 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Comment = <small>(2''S'')-2-amino</small> |
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| EINECS = 211-725-9 |
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| KEGG = <!-- blanked - oldvalue: C02727 --> |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = N-Epsilon-acetyllysine |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 58260 |
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| ChEMBL = <!-- blanked - oldvalue: 1230958 --> |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| Beilstein = 1725438 |
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| Gmelin = 747339 |
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| 3DMet = B01598 |
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| SMILES = CC(=O)NCCCCC(N)C(O)=O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| InChI = 1/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) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DTERQYGMUDWYAZ-ZETCQYMHSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section1={{Chembox Identifiers |
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| CASNo = 692-04-6 |
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| C=8|H=16|N=2|O=3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ExactMass = 188.116092388 g mol<sup>-1</sup> |
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| CASNo_Comment = <small>''S''</small> |
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| MeltingPtC = 250 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Melting_notes = decomposes |
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| LogP = -0.961 |
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| UNII = 470AD5VY1X |
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| UNII_Comment = <small>''S''</small> |
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| pKa = 2.529 |
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| pKb = 11.468 |
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| PubChem = 265949 |
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| PubChem1 = 6994067 |
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| PubChem1_Comment = <small>''R''</small> |
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| PubChem2 = 92832 |
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| PubChem2_Comment = <small>''S''</small> |
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| ChemSpiderID = 233732 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 83801 |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1_Comment = <small>''S''</small> |
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| EINECS = 211-725-9 |
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| KEGG = C02727 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = N-epsilon-acetyllysine |
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| ChEBI = 17752 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1230958 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| Beilstein = 1725438 <small>''S''</small> |
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| Gmelin = 747339 <small>''S''</small> |
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| 3DMet = |
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| SMILES = CC(=O)NCCCC(N)C(=O)O |
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| StdInChI = 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) |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DTERQYGMUDWYAZ-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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| C=8 | H=16 | N=2 | O=3 |
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| Appearance = White crystals |
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| Odor = Odourless |
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| Density = 1.139 g/mL |
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| MeltingPtC = 250 |
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| BoilingPtC = 442 |
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| LogP = −0.961 |
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| pKa = 2.529 |
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| pKb = 11.468 |
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}} |
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}} |
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|Section3={{Chembox Related |
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| OtherFunction_label = alkanoic acids |
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| OtherFunction = ] |
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}} |
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}} |
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'''Acetyllysine''' (or acetylated lysine) is an ]-derivative of the ] ]. There are multiple forms of acetyllysine: this article is about ''N''-ε-acetyl-<small>L</small>-lysine; the other form is ''N''-α-acetyl-<small>L</small>-lysine. |
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In ]s, the ] of lysine residues is an important mechanism of ]. It functions by regulating the binding of ]s to ] in ]s and thereby controlling the expression of genes on that DNA. Non-histone proteins are acetylated as well. Unlike the functionally similar ], acetyllysine does not carry a positive charge on its side chain. |
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] (HATs) catalyze the addition of acetyl groups from ] onto certain lysine residues of histones and non-histone proteins. ] (HDACs) catalyze the removal of acetyl groups from acetylated lysines. |
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Acetyllysine can be synthesized from lysine by the selective ] of the terminal amine group.<ref>For example: {{cite journal | vauthors = Kikugawa, Mitsui, Sakamoto | title = N-methoxydiacetamide: A new selective acetylating agent | journal = Journal Tetrahedron Letters | volume = 31 | issue = 2 | pages = 243–246 | year = 1990 | doi = 10.1016/S0040-4039(00)94382-X}}</ref> |
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==References== |
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{{reflist}} |
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] |
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] |
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] |