Hydroxylysine: Difference between revisions
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{{chembox |
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|ImageFile=Hydroxylysine.png |
| ImageFile = Hydroxylysine.png |
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|ImageSize=200px |
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| IUPACName = (5''R'')-5-Hydroxy-<small>L</small>-lysine |
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| OtherNames = {{bulletedlist|5-Hydroxy-L-lysine|α,ɛ-Diamino-δ-hydroxycaproic acid}} |
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| InChI = 1/C6H14N2O3/c7-4-2-1-3-5(8-11)6(9)10/h5,8,11H,1-4,7H2,(H,9,10) |
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| InChIKey = QJHBJHUKURJDLG-UHFFFAOYAI |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = |
| 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}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = |
| StdInChIKey = YSMODUONRAFBET-UHNVWZDZSA-N |
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| CASNo_Ref = {{cascite|changed|CAS}} |
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| CASNo= |
| CASNo = 1190-94-9 |
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| PubChem=3032849 |
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| SMILES = NCCCCC(NO)C(O)=O |
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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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|Section2= {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=6|H=14|N=2|O=3 |
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| Formula=C<sub>6</sub>H<sub>14</sub>N<sub>2</sub>O<sub>3</sub> |
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| MolarMass=162.187 |
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|Section3= {{Chembox Hazards |
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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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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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It is biosynthesized from lysine via oxidation by the enzyme [[lysyl hydroxylase]]. |
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==References== |
==References== |
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* {{MeshName|Hydroxylysine}} |
* {{MeshName|Hydroxylysine}} |
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[[Category:Amino acids]] |
[[Category:Alpha-Amino acids]] |
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[[cs:Hydroxylysin]] |
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[[de:Hydroxylysin]] |
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[[ja:ヒドロキシリシン]] |
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[[pl:Hydroksylizyna]] |
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[[pt:Hidroxilisina]] |
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[[ru:Гидроксилизин]] |
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Latest revision as of 14:08, 7 October 2023
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| Names | |
|---|---|
| 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)