Hydroxylysine: Difference between revisions
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! {{chembox header}}| '''Hydroxylysine''' |
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| ImageFile = Hydroxylysine.png |
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| ImageSize = 200px |
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| [[Common name]] |
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| IUPACName = (5''R'')-5-Hydroxy-<small>L</small>-lysine |
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| hydroxylysine |
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| OtherNames = {{bulletedlist|5-Hydroxy-L-lysine|α,ɛ-Diamino-δ-hydroxycaproic acid}} |
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| SystematicName = (2''S'',5''R'')-2,6-Diamino-5-hydroxyhexanoic acid |
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| [[IUPAC nomenclature|Systematic name]] |
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| Section1 = {{Chembox Identifiers |
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| 2,6-diamino-5-<br>hydroxyhexanoic acid |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2297721 |
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| [[Chemical formula]] |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| C<sub>6</sub>H<sub>14</sub>N<sub>2</sub>O<sub>3</sub> |
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| StdInChI =1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| [[Molar mass]] |
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| StdInChIKey = YSMODUONRAFBET-UHNVWZDZSA-N |
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| 162.19 g mol<sup>-1</sup> |
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| CASNo_Ref = {{cascite|changed|CAS}} |
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| CASNo = 1190-94-9 |
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| PubChem=3032849 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 2GQB349IUB |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C16741 |
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| SMILES = C(C[C@@H](C(=O)O)N)[C@H](CN)O |
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| MeSHName=Hydroxylysine |
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| C=6|H=14|N=2|O=3 |
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'''Hydroxylysine''' ('''Hyl''') is an [[amino acid]] with the molecular formula C<sub>6</sub>H<sub>14</sub>N<sub>2</sub>O<sub>3</sub>. It was first discovered in 1921 by [[Donald Van Slyke]] as the 5-hydroxylysine form.<ref>{{Cite journal | last1 = Van Slyke | first1 = DD. | last2 = Hiller | first2 = A. | title = An Unidentified Base among the Hydrolytic Products of Gelatin. | journal = Proc Natl Acad Sci U S A | volume = 7 | issue = 7 | pages = 185–6 |date=Jul 1921 | doi = 10.1073/pnas.7.7.185| pmid = 16586836 | pmc=1084845| bibcode = 1921PNAS....7..185V | doi-access = free }}</ref> It arises from a post-translational [[Hydroxyl|hydroxy]] modification of [[lysine]]. It is most widely known as a component of [[collagen]].<ref>[http://herkules.oulu.fi/isbn9514267990/html/x319.html Hydroxylysine] at [[University of Oulu]]</ref> |
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[[Image:Lysine_5_hydroxy.png|thumb|150px|left|Schematic diagram of 5-hydroxylysine.]] |
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It is biosynthesized from lysine via oxidation by [[lysyl hydroxylase]] enzymes. The most common form is the (5''R'') stereoisomer found in collagen. However, the enzyme JMJD6 has recently been shown to be a lysyl hydroxylase which modifies an RNA splicing factor producing the (5''S'') stereoisomer. Additionally, in ''E. coli'', there has been at least one lysine ''N''-hydroxylase enzyme identified, named IucD.<ref>{{Cite journal | last1 = de Lorenzo | first1 = V.| title = Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12. | journal = J. Bacteriol. | volume = 165 | issue = 2 | pages = 570–8 |date=Feb 1986 | pmid = 2935523 | pmc=214457|display-authors=etal| doi = 10.1128/jb.165.2.570-578.1986}}</ref> |
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'''Hydroxylysine''' is an [[amino acid]], C<sub>6</sub>H<sub>14</sub>N<sub>2</sub>O<sub>3</sub>. It is most widely known as a component of [[collagen]]. A standard amino acid with the R' group consisting of an amino terminated butyl hydrocarbon chain, with a hydroxyl group on the carbon atom before the amino group. See also [[lysine]] which lacks the hydroxyl group of hydrolysine. |
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==References== |
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Structure is: [[Amine|NH2]] - [[Hydrocarbon|CH2]] - [[Alcohol|CH(OH)]] - [[Hydrocarbon|CH2]] - [[Hydrocarbon|CH2]] - [[Amino acid|CH(NH2)COOH]] |
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<references/> |
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The number of hydrogens vary depending on the ionization state of the molecule's carboxyl and amino groups. |
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==External links== |
==External links== |
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*[http://herkules.oulu.fi/isbn9514267990/html/x319.html More in depth information about the biological context of hydroxylysine] |
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* {{MeshName|Hydroxylysine}} |
* {{MeshName|Hydroxylysine}} |
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{{ChemicalSources}} |
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[[Category:Amino acids]] |
[[Category:Alpha-Amino acids]] |
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Latest revision as of 14:08, 7 October 2023
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| Names | |
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| IUPAC name
(5R)-5-Hydroxy-L-lysine
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| Systematic IUPAC name
(2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.013.388 |
| KEGG | |
| MeSH | Hydroxylysine |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H14N2O3 | |
| Molar mass | 162.189 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hydroxylysine (Hyl) is an amino acid with the molecular formula C6H14N2O3. It was first discovered in 1921 by Donald Van Slyke as the 5-hydroxylysine form.[1] It arises from a post-translational hydroxy modification of lysine. It is most widely known as a component of collagen.[2]
It is biosynthesized from lysine via oxidation by lysyl hydroxylase enzymes. The most common form is the (5R) stereoisomer found in collagen. However, the enzyme JMJD6 has recently been shown to be a lysyl hydroxylase which modifies an RNA splicing factor producing the (5S) stereoisomer. Additionally, in E. coli, there has been at least one lysine N-hydroxylase enzyme identified, named IucD.[3]
References
[edit]- ^ Van Slyke, DD.; Hiller, A. (Jul 1921). "An Unidentified Base among the Hydrolytic Products of Gelatin". Proc Natl Acad Sci U S A. 7 (7): 185–6. Bibcode:1921PNAS....7..185V. doi:10.1073/pnas.7.7.185. PMC 1084845. PMID 16586836.
- ^ Hydroxylysine at University of Oulu
- ^ de Lorenzo, V.; et al. (Feb 1986). "Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12". J. Bacteriol. 165 (2): 570–8. doi:10.1128/jb.165.2.570-578.1986. PMC 214457. PMID 2935523.
External links
[edit]- Hydroxylysine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)