View source for Hydroxylysine

{{chembox
| Verifiedfields = changed
| verifiedrevid  = 443864195
| ImageFile      = Hydroxylysine.png
| ImageSize      = 200px
| IUPACName      = (5''R'')-5-Hydroxy-<small>L</small>-lysine
| OtherNames     = {{bulletedlist|5-Hydroxy-L-lysine|α,ɛ-Diamino-δ-hydroxycaproic acid}}
| SystematicName = (2''S'',5''R'')-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 =
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}}

'''Hydroxylysine''' ('''Hyl''') is an [[amino acid]] with the molecular formula C<sub>6</sub>H<sub>14</sub>N<sub>2</sub>O<sub>3</sub>. It was first discovered in 1921 by [[Donald Van Slyke]] as the 5-hydroxylysine form.<ref>{{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 }}</ref> It arises from a post-translational [[Hydroxyl|hydroxy]] modification of [[lysine]].  It is most widely known as a component of [[collagen]].<ref>[http://herkules.oulu.fi/isbn9514267990/html/x319.html Hydroxylysine] at [[University of Oulu]]</ref>

It is biosynthesized from lysine via oxidation by [[lysyl hydroxylase]] enzymes.  The most common form is the (5''R'') 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 (5''S'') stereoisomer.  Additionally, in ''E. coli'', there has been at least one lysine ''N''-hydroxylase enzyme identified, named IucD.<ref>{{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}}</ref>

==References==
<references/>

==External links==
* {{MeshName|Hydroxylysine}}

[[Category:Alpha-Amino acids]]