Hydroxylysine: Difference between revisions

Hydroxylysine
Names
	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	28902-93-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	10613296 ;
ECHA InfoCard	100.013.388
MeSH	Hydroxylysine
PubChem CID	3032849;
UNII	2GQB349IUB ;
CompTox Dashboard (EPA)	DTXSID701317083 ;
	InChI InChI=1S/C6H14N2O3/c7-4-2-1-3-5(8-11)6(9)10/h5,8,11H,1-4,7H2,(H,9,10) Key: QJHBJHUKURJDLG-UHFFFAOYSA-N ; InChI=1/C6H14N2O3/c7-4-2-1-3-5(8-11)6(9)10/h5,8,11H,1-4,7H2,(H,9,10) Key: QJHBJHUKURJDLG-UHFFFAOYAI;
	SMILES NCCCCC(NO)C(O)=O;
Properties
Chemical formula	C6H14N2O3
Molar mass	162.187
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Hydroxylysine 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]

It is biosynthesized from lysine via oxidation by lysyl hydroxylase enzymes. The most common form is the (5R) stereoisomer found in collagen. However, 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

^ Van Slyke, DD.; Hiller, A. (1921). "An Unidentified Base among the Hydrolytic Products of Gelatin". Proc Natl Acad Sci U S A. 7 (7): 185–6. doi:10.1073/pnas.7.7.185. PMID 16586836. {{cite journal}}: Unknown parameter |month= ignored (help)
^ Hydroxylysine at University of Oulu
^ de Lorenzo, V.; et al. (1986). "Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12". J. Bacteriol. 165 (2): 570–8. PMID 2935523. {{cite journal}}: Explicit use of et al. in: |first1= (help); Unknown parameter |month= ignored (help)

External links

Hydroxylysine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

[1] Van Slyke, DD.; Hiller, A. (1921). "An Unidentified Base among the Hydrolytic Products of Gelatin". Proc Natl Acad Sci U S A. 7 (7): 185–6. doi:10.1073/pnas.7.7.185. PMID 16586836. {{cite journal}}: Unknown parameter |month= ignored (help)

[2] Hydroxylysine at University of Oulu

[3] Lorenzo, V.; et al. (1986). "Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12". J. Bacteriol. 165 (2): 570–8. PMID 2935523. {{cite journal}}: Explicit use of et al. in: |first1= (help); Unknown parameter |month= ignored (help)

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 '''Hydroxylysine''' 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 | month = Jul | year = 1921 | doi =  10.1073/pnas.7.7.185| pmid = 16586836 }}</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 (5R) stereoisomer found in collagen.  However, 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 <ref>{{Cite journal  | last1 = de Lorenzo | first1 = V., ''et al.'' | 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 | month = Feb | year = 1986 | pmid = 2935523 }}</ref>.
+It is biosynthesized from lysine via oxidation by [[lysyl hydroxylase]] enzymes.  The most common form is the (5R) stereoisomer found in collagen.  However, 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 <ref>{{Cite journal  | last1 = de Lorenzo | first1 = V., ''et al.'' | 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 | month = Feb | year = 1986 | pmid = 2935523 }}</ref>.
 ==References==