hydroxylysine

Hydroxylysine
	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
PubChem	3032849
ChemSpider	10613296
UNII	2GQB349IUB
MeSH	Hydroxylysine
Jmol-3D images	Image 1
	SMILES NCCCCC(NO)C(O)=O ;
	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 ;
Properties
Molecular formula	C6H14N2O3
Molar mass	162.187
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/09/02 13:32:36」(JST)

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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. (Jul 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. PMC 1084845. PMID 16586836. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1084845.
^ 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. PMC 214457. PMID 2935523. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=214457.

External links

Hydroxylysine at the US National Library of Medicine Medical Subject Headings (MeSH)

UpToDate Contents

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English Journal

Isolation and characterization of fish scale collagen from tilapia (Oreochromis sp.) by a novel extrusion-hydro-extraction process.

Huang CY1, Kuo JM2, Wu SJ3, Tsai HT2.
Food chemistry.Food Chem.2016 Jan 1;190:997-1006. doi: 10.1016/j.foodchem.2015.06.066. Epub 2015 Jun 22.
Collagen is highly valued both as a food additive and a functional food ingredient. It is generally extracted by treatments with acid or alkali, enzyme, and microorganisms. However these methods are generally batch type, time-, energy-, reactant-, and cost-consuming. Extrusion is widely used in the
PMID 26213067

Genetic basis of alpha-aminoadipic and alpha-ketoadipic aciduria.

Hagen J1, Te Brinke H, Wanders RJ, Knegt AC, Oussoren E, Hoogeboom AJ, Ruijter GJ, Becker D, Schwab KO, Franke I, Duran M, Waterham HR, Sass JO, Houten SM.
Journal of inherited metabolic disease.J Inherit Metab Dis.2015 Sep;38(5):873-9. doi: 10.1007/s10545-015-9841-9. Epub 2015 Apr 10.
Alpha-aminoadipic and alpha-ketoadipic aciduria is an autosomal recessive inborn error of lysine, hydroxylysine, and tryptophan degradation. To date, DHTKD1 mutations have been reported in two alpha-aminoadipic and alpha-ketoadipic aciduria patients. We have now sequenced DHTKD1 in nine patients dia
PMID 25860818

The Ancient Immunoglobulin Domains of Peroxidasin Are Required to Form Sulfilimine Cross-links in Collagen IV.

Ero-Tolliver IA1, Hudson BG2, Bhave G3.
The Journal of biological chemistry.J Biol Chem.2015 Aug 28;290(35):21741-8. doi: 10.1074/jbc.M115.673996. Epub 2015 Jul 15.
The collagen IV sulfilimine cross-link and its catalyzing enzyme, peroxidasin, represent a dyad critical for tissue development, which is conserved throughout the animal kingdom. Peroxidasin forms novel sulfilimine bonds between opposing methionine and hydroxylysine residues to structurally reinforc
PMID 26178375

Japanese Journal

1P-104 微生物由来新規リジン水酸化酵素の発見(酵素学,酵素工学,一般講演)

原良太郎,山縣海,三宅良磨,川端潤,木野邦器
日本生物工学会大会講演要旨集 66, 43, 2014-08-05
NAID 110009906185

Isolation of collagen from tiger pufferfish parts and its solubility in dilute acetic acid

TSUKAMOTO Hiroshi,YOKOYAMA Yoshihiro,SUZUKI Tohru,MIZUTA Shoshi,YOSHINAKA Reiji,AKAHANE Yoshiaki
Fisheries science : FS 79(5), 857-864, 2013-09-01
NAID 10031191439

Isolation of collagen from tiger pufferfish parts and its solubility in dilute acetic acid

Tsukamoto Hiroshi,Yokoyama Yoshihiro,Suzuki Tohru [他]
Fisheries science 79(5), 857-864, 2013-09
NAID 40019790263

Related Pictures

[0] 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. doi:10.1073/pnas.7.7.185. PMC 1084845. PMID 16586836. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1084845.

[1] Hydroxylysine at University of Oulu

[2] 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. PMC 214457. PMID 2935523. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=214457.

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