Hydroxylysine

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.388 Edit this at Wikidata
KEGG
MeSH Hydroxylysine
UNII
  • 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 checkY
    Key: YSMODUONRAFBET-UHNVWZDZSA-N checkY
  • C(C[C@@H](C(=O)O)N)[C@H](CN)O
Properties
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 checkY☒N ?)
Close

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]

References

External links

Related Articles

Wikiwand AI