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]
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| Names | |
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| IUPAC name
(5R)-5-Hydroxy-L-lysine | |
| 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 |
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| ECHA InfoCard | 100.013.388 
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| KEGG |
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| 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). | |
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]
