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Hydroxylysine

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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.388 Edit this at Wikidata
KEGG
MeSH Hydroxylysine
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: YSMODUONRAFBET-UHNVWZDZSA-N
SMILES
  • C(C(C(=O)O)N)(CN)O
Properties
Chemical formula C6H14N2O3
Molar mass 162.189 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. It arises from a post-translational hydroxy modification of lysine. It is most widely known as a component of collagen.

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.

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. Bibcode:1921PNAS....7..185V. 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. doi:10.1128/jb.165.2.570-578.1986. PMC 214457. PMID 2935523.

External links

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