デスモシン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/29 01:50:57」(JST)
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This article does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (November 2006) |
| Desmosine |
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IUPAC name
6-{4-[(4S)-4-Amino-4-carboxybutyl]-3,5-bis[(3S)-3-amino-3-carboxypropyl]-1-pyridiniumyl}-L-norleucine
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| Identifiers |
| CAS number |
11003-57-9 Y |
| PubChem |
25435 |
| ChemSpider |
13085543 N |
| Jmol-3D images |
Image 1 |
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O=C(O)[C@@H](N)CCCC[n+]1cc(c(c(c1)CC[C@@H](C(=O)O)N)CCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
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InChI=1S/C24H39N5O8/c25-17(21(30)31)5-1-2-11-29-12-14(7-9-19(27)23(34)35)16(4-3-6-18(26)22(32)33)15(13-29)8-10-20(28)24(36)37/h12-13,17-20H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1 Y
Key: VEVRNHHLCPGNDU-MUGJNUQGSA-O N
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| Properties |
| Molecular formula |
C24H40N5O8 |
| Molar mass |
526.60 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| N (verify) (what is: Y/N?) |
| Infobox references |
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A desmosine cross-link is formed from three allysyl side chains plus one unaltered lysyl side chain from the same or neighbouring polypeptides. Detection of desmosine in urine, plasma or sputum samples can be a marker for elastin breakdown due to high elastase activity related to certain diseases. [1] [2]
It is found in elastin. Desmosine causes a yellow color.
This desmosine is responsible for the rubber properties of elastin.
References
- ^ Millipore product catalogue, purified desmosine http://www.millipore.com/catalogue/item/263275-5mg
- ^ Ma, Turino and Lin, J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Jul 1;879(21):1893-8, Quantitation of Desmosine and Isodesmosine in Urine, Plasma and Sputum by LC-MS/MS as biomarkers for elastin degradation, http://www.ncbi.nlm.nih.gov/pubmed/21621489
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Protein primary structure and posttranslational modifications
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| General |
- Peptide bond
- Protein biosynthesis
- Proteolysis
- Racemization
- N-O acyl shift
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| N terminus |
- Acetylation
- Carbamylation
- Formylation
- Glycation
- Methylation
- Myristoylation (Gly)
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| C terminus |
- Amidation
- Glycosyl phosphatidylinositol (GPI)
- O-methylation
- Detyrosination
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| Single specific AAs |
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Serine/Threonine
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- Phosphorylation
- Dephosphorylation
- Glycosylation
- Methylidene-imidazolone (MIO) formation
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Tyrosine
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- Phosphorylation
- Dephosphorylation
- Sulfation
- Porphyrin ring linkage
- Adenylylation
- Flavin linkage
- Topaquinone (TPQ) formation
- Detyrosination
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Cysteine
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- Palmitoylation
- Prenylation
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Aspartate
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Glutamate
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- Carboxylation
- Methylation
- Polyglutamylation
- Polyglycylation
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Asparagine
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- Deamidation
- Glycosylation
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Glutamine
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Lysine
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- Methylation
- Acetylation
- Acylation
- Adenylylation
- Hydroxylation
- Ubiquitination
- Sumoylation
- ADP-ribosylation
- Deamination
- Oxidative deamination to aldehyde
- O-glycosylation
- Imine formation
- Glycation
- Carbamylation
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Arginine
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- Citrullination
- Methylation
- ADP-ribosylation
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Proline
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Histidine
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- Diphthamide formation
- Adenylylation
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Tryptophan
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| Crosslinks between two AAs |
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Cysteine-Cysteine
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Methionine-Hydroxylysine
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Lysine-Tyrosylquinone
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- Lysine tyrosylquinone (LTQ) formation
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Tryptophan-Tryptophylquinone
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- Tryptophan tryptophylquinone (TTQ) formation
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Three consecutive AAs
(chromophore formation) |
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Serine–Tyrosine–Glycine
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- p-Hydroxybenzylidene-imidazolinone formation
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Histidine–Tyrosine–Glycine
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- 4-(p-hydroxybenzylidene)-5-imidazolinone formation
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| Crosslinks between four AAs |
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Allysine-Allysine-Allysine-Lysine
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←Amino acids
Secondary structure→
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English Journal
- Long-term Variability of Desmosine/Isodesmosine as Biomarker in Alpha-1-antritrypsin Deficiency-related COPD.
- Fregonese L, Ferrari F, Fumagalli M, Luisetti M, Stolk J, Iadarola P.SourcePulmonology, Leiden University Medical Centre, Leiden, Netherlands, 1.
- COPD.COPD.2011 Oct;8(5):329-33. Epub 2011 Jul 27.
- Desmosine and isodesmosine are products of elastin breakdown which are candidate biomarkers to measure lung destruction in COPD. Data exist on the burden of desmosines in urine and plasma in COPD but long-term changes have never been investigated. We determined the changes of desmosine levels over 1
- PMID 21793711
- Cation exchange HPLC analysis of desmosines in elastin hydrolysates.
- Per?a-Kajan J, Gryszczy?ska A, Mielcarek S, Jakubowski H.SourceDepartment of Biochemistry and Biotechnology, Pozna? University of Life Sciences, 60-637, Pozna?, Poland, kajan@up.poznan.pl.
- Analytical and bioanalytical chemistry.Anal Bioanal Chem.2011 Sep 2. [Epub ahead of print]
- Desmosine crosslinks are responsible for the elastic properties of connective tissues in lungs and cardiovascular system and are often compromised in disease states. We developed a new, fast, and simple cation exchange HPLC assay for the analysis of desmosine and isodesmosine in animal elastin. The
- PMID 21887606
Japanese Journal
- Synthetic Study of Desmosine and Isodesmosine, Crosslinking Amino Acids of Elastin
- KOSEKI Yohei,YANUMA Hiroto,HAYASHI Takahiro,YAMADA Haruka,LIN Yong Y.,USUKI Toyonobu
- Peptide science : proceedings of the ... Japanese Peptide Symposium 2010, 195, 2011-03-01
- NAID 10028237815
- Development of a Robust LC-MS/MS Method for Determination of Desmosine and Isodesmosine in Human Urine
- Shiraishi Kohei,Matsuzaki Kazue,Matsumoto Akinori,Hashimoto Yuuki,Iba Kazuhiko
- Journal of Oleo Science 59(8), 431-439, 2010
- … Desmosine (DES) and isodesmosine (IDES) are both pyridinium amino acid isomers that serve as cross-linking molecules binding the polymeric chains of amino acids into elastin. …
- NAID 130000301377
- ブタ由来エラスチンペプチドの経口摂取によるマウス皮膚水分含量の向上
- 早川 徹,佐藤 三佳子,雜賀（江草） 愛,高畑 能久,森松 文毅,野村 義宏
- 日本畜産学会報 80(2), 215-222, 2009
- ブタ大動脈よりエラスチンの酵素加水分解ペプチド（エラスチンペプチド）を調製し，その摂取が皮膚にもたらす影響について検討した．生後7週の雄ヘアレスマウスにエラスチンペプチドなどの試料を経口投与し，63日間の飼育を行った．皮膚老化モデルとして光老化モデルを採用し，週3回の頻度で紫外線を照射した．照射52日目および55日目にエラスチンペプチドとコラーゲンペプチドを混合投与した群およびコラーゲンペプチド投 …
- NAID 130000117349
Related Links
- Desmosine is in his opinion the most useful and promising pneumoprotein in COPD. Email Michiel Spanbroek, M.D. Michiel Spanbroek, M.D. Michiel Spanbroek was trained in respiratory medicine, and is practicing as a Email ...
- desmosine special amino acid, derived from four lysine residues, and found only in elastin. Allows elastin to stretch reversibly in all directions. des·mo·sine (des'mō-sēn), A cross-linking amino acid formed from lysyl residues found in ...
Related Pictures
