IUPAC name
(2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid
Other names
α,ɛ-diamino-δ-hydroxycaproic acid
1190-94-9 N
3D model (Jmol) Interactive image
ChemSpider 10613296 YesY
ECHA InfoCard 100.025.309
KEGG C16741 N
MeSH Hydroxylysine
PubChem 3032849
Molar mass 162.187
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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, 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]


  1. 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. doi:10.1073/pnas.7.7.185. PMC 1084845Freely accessible. PMID 16586836.
  2. Hydroxylysine at University of Oulu
  3. 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. PMC 214457Freely accessible. PMID 2935523.
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