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Hydroxylysine

From Wikipedia, the free encyclopedia
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 InfoCard100.013.388Edit this at Wikidata
KEGG
MeSHHydroxylysine
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 mass162.189 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Hydroxylysine (Hyl) is anamino acid with the molecular formula C6H14N2O3. It was first discovered in 1921 byDonald Van Slyke as the 5-hydroxylysine form.[1] It arises from a post-translationalhydroxy modification oflysine. It is most widely known as a component ofcollagen.[2]

It is biosynthesized from lysine via oxidation bylysyl 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, inE. coli, there has been at least one lysineN-hydroxylase enzyme identified, named IucD.[3]

References

[edit]
  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. ^HydroxylysineArchived 2012-11-20 at theWayback Machine atUniversity 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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