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
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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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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)