hydroxylysine

{{chembox

| Verifiedfields = changed

| verifiedrevid = 443864195

| ImageFile = Hydroxylysine.png

| ImageSize = 200px

| IUPACName = (5R)-5-Hydroxy-L-lysine

| OtherNames = {{bulletedlist|5-Hydroxy-L-lysine|α,ɛ-Diamino-δ-hydroxycaproic acid}}

| SystematicName = (2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2297721

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI =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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = YSMODUONRAFBET-UHNVWZDZSA-N

| CASNo_Ref = {{cascite|changed|CAS}}

| CASNo = 1190-94-9

| PubChem=3032849

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2GQB349IUB

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C16741

| SMILES = C(C[C@@H](C(=O)O)N)[C@H](CN)O

| MeSHName=Hydroxylysine

}}

| Section2 = {{Chembox Properties

| C=6|H=14|N=2|O=3

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

| Section3 = {{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

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.{{Cite journal | last1 = Van Slyke | first1 = DD. | last2 = Hiller | first2 = A. | title = An Unidentified Base among the Hydrolytic Products of Gelatin. | journal = Proc Natl Acad Sci U S A | volume = 7 | issue = 7 | pages = 185–6 |date=Jul 1921 | doi = 10.1073/pnas.7.7.185| pmid = 16586836 | pmc=1084845| bibcode = 1921PNAS....7..185V | doi-access = free }} It arises from a post-translational hydroxy modification of lysine. It is most widely known as a component of collagen.[http://herkules.oulu.fi/isbn9514267990/html/x319.html Hydroxylysine] at University of Oulu

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.{{Cite journal | last1 = de Lorenzo | first1 = V.| title = Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12. | journal = J. Bacteriol. | volume = 165 | issue = 2 | pages = 570–8 |date=Feb 1986 | pmid = 2935523 | pmc=214457|display-authors=etal| doi = 10.1128/jb.165.2.570-578.1986}}