epsilon-(gamma-Glutamyl)lysine (BioDeep_00000014221)

 

Secondary id: BioDeep_00001869359, BioDeep_00001872671, BioDeep_00001894379

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid

化学式: C11H21N3O5 (275.1481136)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 0.09%

分子结构信息

SMILES: C(CCNC(=O)CCC(C(=O)O)N)CC(C(=O)O)N
InChI: InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

描述信息

In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688). In Parkinsons disease (PD), conformational changes in the alpha-synuclein monomer precede the formation of Lewy bodies. Both tTG and its substrate-characteristic N(epsilon)-(gamma-glutamyl)-lysine crosslink are increased in PD nigral dopamine neurons. (PMID 15001552). Expression of tissue transglutaminase (tTgase) and epsilon-(gamma-glutamyl)-lysine was present in all scarring of the blebs sites, being the main cause of failure in glaucoma filtration surgery. Transglutaminases are calcium-dependent enzymes that catalyze the posttranslational modification of proteins through an acyl transfer reaction between the gamma-carboxamide group of a peptide-bound glutaminyl residue and various amines. Covalent cross-linking using epsilon-(gamma-glutamyl)-lysine bonds is stable and resistant to enzymatic, chemical, and mechanical disruption. (PMID: 16936095).
In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688)

同义名列表

37 个代谢物同义名

(2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid; epsilon-(gamma-Glutamyl)lysine isodipeptide; epsilonN-(gamma-L-Glutamyl)-L-lysine; epsilon-(gamma-L-Glutamyl)-L-lysine; epsilon-(L-gamma-Glutamyl)-L-lysine; N(epsilon)-(gamma-Glutamyl)-lysine; N-epsilon-(gamma-L-Glutamyl)lysine; Nepsilon-(gamma-Glutamyl)-L-lysine; L-gamma-Glutamyl-L-epsilon-lysine; epsilon-(gamma-L-Glutamyl)lysine; epsilon-(gamma-Glutamyl)-lysine; epsilon-(g-L-Glutamyl)-L-lysine; epsilon-(L-g-Glutamyl)-L-lysine; epsilon-(gamma-Glutamyl)lysine; N(epsilon)-(g-Glutamyl)-lysine; N(6)-L-gamma-Glutamyl-L-lysine; Nepsilon(gamma-Glutamyl)lysine; L-g-Glutamyl-L-epsilon-lysine; gamma-Glutamyl-epsilon-lysine; N6-L-gamma-Glutamyl-L-lysine; Epsilon-(g-Glutamyl)-lysine; εN-(γ-L-Glutamyl)-L-lysine; epsilon-(g-Glutamyl)lysine; N(6)-L-g-Glutamyl-L-lysine; ε-(L-γ-Glutamyl)-L-lysine; ε-(γ-L-Glutamyl)-L-lysine; g-Glutamyl-epsilon-lysine; Nε-(γ-Glutamyl)-L-lysine; N6-L-γ-Glutamyl-L-lysine; epsilon-(gamma-Glu)-lys; ε-(γ-L-Glutamyl)lysine; gamma-Glu-epsilon-Lys; ε-(γ-Glutamyl)lysine; Nε(γ-Glutamyl)lysine; γ-Glutamyl-ε-lysine; g-Glu-epsilon-lys; GGEL peptide



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Michelle Da Silva Lodge, Nick Pullen, Miguel Pereira, Timothy S Johnson. Urinary levels of pro-fibrotic transglutaminase 2 (TG2) may help predict progression of chronic kidney disease. PloS one. 2022; 17(1):e0262104. doi: 10.1371/journal.pone.0262104. [PMID: 35041708]
  • Badri Shrestha, Imran Butt, Michelle Da Silva, Armando Sanchez-Lara, Bart Wagner, Andrew Raftery, Timothy Johnson, John Haylor. Upregulation of transglutaminase and ε (γ-glutamyl)-lysine in the Fisher-Lewis rat model of chronic allograft nephropathy. BioMed research international. 2014; 2014(?):651608. doi: 10.1155/2014/651608. [PMID: 25143942]
  • Chee-Yuen Gan, Lai-Hoong Cheng, Baharin Azahari, Azhar Mat Easa. In-vitro digestibility and amino acid composition of soy protein isolate cross-linked with microbial transglutaminase followed by heating with ribose. International journal of food sciences and nutrition. 2009; 60 Suppl 7(?):99-108. doi: 10.1080/09637480802635090. [PMID: 19194813]
  • Senyan Liu, Yuehong Li, Huiying Zhao, Dong Chen, Qiang Huang, Suxia Wang, Wanzhong Zou, Youkang Zhang, Xiaomei Li, Haichang Huang. Increase in extracellular cross-linking by tissue transglutaminase and reduction in expression of MMP-9 contribute differentially to focal segmental glomerulosclerosis in rats. Molecular and cellular biochemistry. 2006 Mar; 284(1-2):9-17. doi: 10.1007/s11010-005-9005-6. [PMID: 16477388]
  • Christian Schäfer, Michael Schott, Fritz Brandl, Sybille Neidhart, Reinhold Carle. Identification and quantification of epsilon-(gamma-glutamyl)lysine in digests of enzymatically cross-linked leguminous proteins by high-performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS). Journal of agricultural and food chemistry. 2005 Apr; 53(8):2830-7. doi: 10.1021/jf048190a. [PMID: 15826026]
  • Nicholas J Skill, Timothy S Johnson, Ian G C Coutts, Robert E Saint, Marie Fisher, Linghong Huang, A Meguid El Nahas, Russell J Collighan, Martin Griffin. Inhibition of transglutaminase activity reduces extracellular matrix accumulation induced by high glucose levels in proximal tubular epithelial cells. The Journal of biological chemistry. 2004 Nov; 279(46):47754-62. doi: 10.1074/jbc.m402698200. [PMID: 15326185]
  • Vincent Thomas, Guy Fournet, Frantz Simonet, Anne-Marie Roch, Ismaïl Ceylan, Saïd El Alaouia, Gerard Quash. Definition of the fine specificity of the monoclonal antibody 81D4: its reactivity with lysine and polyamine isopeptide cross-links. Journal of immunological methods. 2004 Sep; 292(1-2):83-95. doi: 10.1016/j.jim.2004.06.013. [PMID: 15350514]
  • Timothy S Johnson, Hamdy Abo-Zenah, James N Skill, Samantha Bex, Graham Wild, Colin B Brown, Martin Griffin, A Meguid El Nahas. Tissue transglutaminase: a mediator and predictor of chronic allograft nephropathy?. Transplantation. 2004 Jun; 77(11):1667-75. doi: 10.1097/01.tp.0000131171.67671.3c. [PMID: 15201665]
  • A M El Nahas, H Abo-Zenah, N J Skill, S Bex, G Wild, M Griffin, T S Johnson. Elevated epsilon-(gamma-glutamyl)lysine in human diabetic nephropathy results from increased expression and cellular release of tissue transglutaminase. Nephron. Clinical practice. 2004; 97(3):c108-17. doi: 10.1159/000078639. [PMID: 15292688]
  • Alessandra Amendola, Laszlo Fesus, Mauro Piacentini, Zsuzsa Szondy. 'Tissue' transglutaminase in AIDS. Journal of immunological methods. 2002 Jul; 265(1-2):145-59. doi: 10.1016/s0022-1759(02)00077-7. [PMID: 12072185]
  • Jedidah W Danson, Mary Lynn Trawick, Arthur J L Cooper. Spectrophotometric assays for L-lysine alpha-oxidase and gamma-glutamylamine cyclotransferase. Analytical biochemistry. 2002 Apr; 303(2):120-30. doi: 10.1006/abio.2002.5587. [PMID: 11950211]
  • N J Skill, M Griffin, A M El Nahas, T Sanai, J L Haylor, M Fisher, M F Jamie, N N Mould, T S Johnson. Increases in renal epsilon-(gamma-glutamyl)-lysine crosslinks result from compartment-specific changes in tissue transglutaminase in early experimental diabetic nephropathy: pathologic implications. Laboratory investigation; a journal of technical methods and pathology. 2001 May; 81(5):705-16. doi: 10.1038/labinvest.3780279. [PMID: 11351042]
  • D Monti, S Salvioli, M Capri, W Malorni, E Straface, A Cossarizza, B Botti, M Piacentini, G Baggio, C Barbi, S Valensin, M Bonafè, C Franceschi. Decreased susceptibility to oxidative stress-induced apoptosis of peripheral blood mononuclear cells from healthy elderly and centenarians. Mechanisms of ageing and development. 2000 Dec; 121(1-3):239-50. doi: 10.1016/s0047-6374(00)00220-7. [PMID: 11164477]
  • T S Johnson, M Griffin, G L Thomas, J Skill, A Cox, B Yang, B Nicholas, P J Birckbichler, C Muchaneta-Kubara, A Meguid El Nahas. The role of transglutaminase in the rat subtotal nephrectomy model of renal fibrosis. The Journal of clinical investigation. 1997 Jun; 99(12):2950-60. doi: 10.1172/jci119490. [PMID: 9185519]
  • K Seguro, Y Kumazawa, C Kuraishi, H Sakamoto, M Motoki. The epsilon-(gamma-glutamyl)lysine moiety in crosslinked casein is an available source of lysine for rats. The Journal of nutrition. 1996 Oct; 126(10):2557-62. doi: 10.1093/jn/126.10.2557. [PMID: 8857517]
  • A M Walker, D W Montgomery, S Saraiya, T W Ho, H S Garewal, J Wilson, L Lorand. Prolactin-immunoglobulin G complexes from human serum act as costimulatory ligands causing proliferation of malignant B lymphocytes. Proceedings of the National Academy of Sciences of the United States of America. 1995 Apr; 92(8):3278-82. doi: 10.1073/pnas.92.8.3278. [PMID: 7724552]
  • R H Rice, V J Wong, K E Pinkerton. Ultrastructural visualization of cross-linked protein features in epidermal appendages. Journal of cell science. 1994 Jul; 107 ( Pt 7)(?):1985-92. doi: 10.1242/jcs.107.7.1985. [PMID: 7983163]
  • J Harsfalvi, E Tarcsa, M Udvardy, G Zajka, T Szarvas, L Fesus. Presence and possible origin of epsilon(gamma-glutamyl)lysine isodipeptide in human plasma. Thrombosis and haemostasis. 1992 Jan; 67(1):60-2. doi: NULL. [PMID: 1615484]
  • L Fesus, E Tarcsa, N Kedei, F Autuori, M Piacentini. Degradation of cells dying by apoptosis leads to accumulation of epsilon(gamma-glutamyl)lysine isodipeptide in culture fluid and blood. FEBS letters. 1991 Jun; 284(1):109-12. doi: 10.1016/0014-5793(91)80773-v. [PMID: 1676376]
  • E Cocuzzi, W C Breckenridge. The biochemistry of epsilon-amino groups of lysine residues from apolipoprotein B of human low density lipoprotein. Atherosclerosis. 1986 Jul; 61(1):25-34. doi: 10.1016/0021-9150(86)90110-3. [PMID: 3730052]
  • L A Goldsmith. Human epidermal transglutaminase. The Journal of investigative dermatology. 1983 Jun; 80 Suppl(?):39s-41s. doi: NULL. [PMID: 6133898]
  • M L Fink, J E Folk. gamma-Glutamylamine cyclotransferase. An enzyme involved in the catabolism of epsilon-(gamma-glutamyl)lysine and other gamma-glutamylamines. Molecular and cellular biochemistry. 1981 Aug; 38 Spec No(Pt 1):59-67. doi: 10.1007/bf00235688. [PMID: 6117008]
  • E J Squires, L A Feltham. Isolation, characterization and seasonal variations in the concentration of N-epsilon-(gamma-glutamyl)-lysine isodipeptide in the blood plasma of the winter flounder (Pseudopleuronectes americanus). The Biochemical journal. 1980 Mar; 185(3):761-6. doi: 10.1042/bj1850761. [PMID: 7387633]