Hydroxylysine

Names
IUPAC name (5R)-5-Hydroxy-L-lysine
Systematic 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	1190-94-9 N
3D model (JSmol)	Interactive image
ChemSpider	2297721 Y
ECHA InfoCard	100.013.388
KEGG	C16741 N
MeSH	Hydroxylysine
PubChem CID	3032849
UNII	2GQB349IUB Y
InChI InChI=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 Y Key: YSMODUONRAFBET-UHNVWZDZSA-N Y
SMILES C(C[C@@H](C(=O)O)N)[C@H](CN)O
Properties
Chemical formula	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). N verify (what is YN ?) 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, 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]