| Revision as of 05:22, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444384147 of page Allysine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 09:01, 3 October 2023 edit Kupirijo (talk | contribs)Extended confirmed users9,131 edits semialdehyde |
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{{distinguish|Allicin}} |
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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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| verifiedrevid = 443378000 |
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|ImageFile=Allysine.svg |
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| verifiedrevid = 477318310 |
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| ImageFile=Allysine.svg |
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|IUPACName=2-amino-6-oxo-hexanoic acid |
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| ImageAlt = Skeletal formula of ] |
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|OtherNames=2-aminoadipate semialdehyde, 2-amino-5-formylvaleric acid, norvaline, 6-oxo-DL-norleucine |
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| ImageFile1 = L-Allysine-zwitterion-3D-balls.png |
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|Section1= {{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model of the L-allysine molecule as a zwitteiron |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| PIN = (2''S'')-2-Amino-6-oxohexanoic acid |
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| OtherNames=2-aminoadipate semialdehyde, 2-amino-5-formylvaleric acid, norvaline, 6-oxo-DL-norleucine |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C04076 |
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| KEGG = C04076 |
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| InChI = 1/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)/t5-/m0/s1 |
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| InChI = 1/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)/t5-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GFXYTQPNNXGICT-UHFFFAOYSA-N |
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| StdInChIKey = GFXYTQPNNXGICT-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 1962-83-0 --> |
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| CASNo=1962-83-0 |
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| PubChem=207 |
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| CASNo_Comment = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo1 = 6665-12-9 |
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| CASNo1_Comment = L-enantiomer |
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| PubChem=207 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 202 |
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| ChemSpiderID = 202 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 425I4Y24YZ |
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| UNII = 425I4Y24YZ |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 57988 |
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| ChEBI = 57988 |
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| SMILES = O=CCCC(N)C(=O)O |
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| SMILES = O=CCCC(N)C(=O)O |
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| MeSHName=allysine |
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| MeSHName=allysine |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6 | H=11 | N=1 | O=3 |
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| Formula=C<sub>6</sub>H<sub>11</sub>NO<sub>3</sub> |
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| Appearance= unstable |
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| MolarMass=145.156 |
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| Density=1.74g/cm<sup>3</sup> |
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| MeltingPt= |
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| Density=1.74g/cm3 |
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| BoilingPtC=295.2 |
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| BoilingPt=295.2°C @ 760mmHg |
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|Section3= {{Chembox Hazards |
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| FlashPt=132.3°C |
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| FlashPtC = 132.3 |
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'''Allysine''' is a derivative of ] that features a formyl group in place of the terminal amine. The free amino acid does not exist, but the allysine ''residue'' does. It is produced by aerobic oxidation of lysine residues by the enzyme ]. The transformation is an example of a ]. The ] form exists in equilibrium with a cyclic derivative.<ref name= Stadtman>{{cite journal |doi=10.1007/s00726-003-0012-1 |title=Recent Advances in the Analysis of Oxidized Proteins |year=2003 |last1=Requena |first1=J. R. |last2=Levine |first2=R. L. |last3=Stadtman |first3=E. R. |journal=Amino Acids |volume=25 |issue=3–4 |pages=221–226 |pmid=14661085 |s2cid=28837698 }}</ref> |
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Allysine is involved in the production of ] and ].<ref name=":0">{{cite journal | doi = 10.1146/annurev.bi.53.070184.003441| title = Cross-Linking in Collagen and Elastin| year = 1984| last1 = Eyre| first1 = David R.| last2 = Paz| first2 = Mercedes A.| last3 = Gallop| first3 = Paul M.| journal = Annual Review of Biochemistry| volume = 53| pages = 717–748| pmid = 6148038}}</ref> Increased allysine concentration in tissues has been correlated to the presence of fibrosis.<ref>{{cite journal | vauthors = Wahsner J, Désogère P, Abston E, Graham-O'Regan KA, Wang J, Rotile NJ, Schirmer MD, Santos Ferreira DD, Sui J, Fuchs BC, Lanuti M, Caravan P | display-authors = 6 | title = <sup>68</sup>Ga-NODAGA-Indole: An Allysine-Reactive Positron Emission Tomography Probe for Molecular Imaging of Pulmonary Fibrogenesis | journal = Journal of the American Chemical Society | volume = 141 | issue = 14 | pages = 5593–5596 | date = April 2019 | pmid = 30908032 | pmc = 6494104 | doi = 10.1021/jacs.8b12342 }}</ref> |
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Allysine residues react with sodium 2-naphthol-6-sulfonate to produce a ] bis-naphtol-allysine product.<ref>{{cite journal | vauthors = Waghorn PA, Oliveira BL, Jones CM, Tager AM, Caravan P | title = High sensitivity HPLC method for determination of the allysine concentration in tissue by use of a naphthol derivative | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 1064 | pages = 7–13 | date = October 2017 | pmid = 28886479 | pmc = 5662445 | doi = 10.1016/j.jchromb.2017.08.032 }}</ref> In another assay, allysine-containing proteins are reduced with sodium borohydride to give a peptide containing the 6-hydroxynorleucine (6-hydroxy-2-amino]) residue, which (unlike allysine) is stable to proteolysis.<ref name= Stadtman/> |
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==Further reading== |
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*{{cite journal | vauthors = Luna C, Estévez M | title = Formation of allysine in β-lactoglobulin and myofibrillar proteins by glyoxal and methylglyoxal: Impact on water-holding capacity and in vitro digestibility | journal = Food Chemistry | volume = 271 | pages = 87–93 | date = January 2019 | pmid = 30236745 | doi = 10.1016/j.foodchem.2018.07.167 | s2cid = 52309183 }} |
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*{{cite journal | vauthors = Luna C, Arjona A, Dueñas C, Estevez M | title = Allysine and α-Aminoadipic Acid as Markers of the Glyco-Oxidative Damage to Human Serum Albumin under Pathological Glucose Concentrations | journal = Antioxidants | volume = 10 | issue = 3 | pages = 474 | date = March 2021 | pmid = 33802856 | pmc = 8002732 | doi = 10.3390/antiox10030474 | doi-access = free }} |
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== See also == |
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* ] |
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== References == |
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{{reflist}} |
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{{Amino acid metabolism intermediates}} |
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] |
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] |
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] |
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{{Biochemistry-stub}} |