Hydroxylysine

Hydroxylysine
IUPAC name (2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid
Other names 5-Hydroxy-L-lysine, α,ɛ-diamino-δ-hydroxycaproic acid
Identifiers
CAS number	28902-93-4 Y
PubChem	3032849
ChemSpider	10613296 Y
UNII	2GQB349IUB Y
MeSH	Hydroxylysine
Jmol-3D images	Image 1
SMILES NCCCCC(NO)C(O)=O
InChI InChI=1S/C6H14N2O3/c7-4-2-1-3-5(8-11)6(9)10/h5,8,11H,1-4,7H2,(H,9,10) Y Key: QJHBJHUKURJDLG-UHFFFAOYSA-N Y InChI=1/C6H14N2O3/c7-4-2-1-3-5(8-11)6(9)10/h5,8,11H,1-4,7H2,(H,9,10) Key: QJHBJHUKURJDLG-UHFFFAOYAI
Properties
Molecular formula	C6H14N2O3
Molar mass	162.187
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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]

References

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 1084845. 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 214457. PMID 2935523. 

External links

• Hydroxylysine at the US National Library of Medicine Medical Subject Headings (MeSH)