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	1190-94-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	2297721 ;
ECHA InfoCard	100.013.388
KEGG	C16741 ;
MeSH	Hydroxylysine
PubChem CID	3032849;
UNII	2GQB349IUB ;
CompTox Dashboard (EPA)	DTXSID701317083 ;
	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/s1 Key: YSMODUONRAFBET-UHNVWZDZSA-N ;
	SMILES C(C[C@@H](C(=O)O)N)[C@H](CN)O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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Revision as of 16:15, 21 December 2019

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]

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

^ 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.
^ Hydroxylysine at University of Oulu
^ 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

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

[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] 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.

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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}}</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>
+'''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 }}</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}}</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==