N(6)-(1-Carboxyethyl)-L-lysine (BioDeep_00000847056)
代谢物信息卡片
N(6)-(1-Carboxyethyl)-L-lysine
化学式: C9H18N2O4 (218.1266508)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C(=O)O)NCCCCC(C(=O)O)N
InChI: InChI=1S/C9H18N2O4/c1-6(8(12)13)11-5-3-2-4-7(10)9(14)15/h6-7,11H,2-5,10H2,1H3,(H,12,13)(H,14,15)/t6?,7-/m0/s1
描述信息
A L-lysine derivative formed during the reaction between methylglyoxal and protein. CEL is a homologue of N(epsilon)-(carboxymethyl)lysine (CML), an advanced glycation end-product that is formed on reaction of glyoxal or glycolaldehyde with protein and on oxidative cleavage of fructoselysine, the Amadori adduct formed on glycation of protein by glucose.
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代谢反应
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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。
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文献列表
- Yoona Kim, Jennifer B Keogh, Permal Deo, Peter M Clifton. Differential Effects of Dietary Patterns on Advanced Glycation end Products: A Randomized Crossover Study.
Nutrients.
2020 Jun; 12(6):. doi:
10.3390/nu12061767. [PMID: 32545555] - Antonio Dario Troise, Markus Wiltafsky, Vincenzo Fogliano, Paola Vitaglione. The quantification of free Amadori compounds and amino acids allows to model the bound Maillard reaction products formation in soybean products.
Food chemistry.
2018 May; 247(?):29-38. doi:
10.1016/j.foodchem.2017.12.019. [PMID: 29277225] - Sylwia Mildner-Szkudlarz, Aleksander Siger, Artur Szwengiel, Krzysztof Przygoński, Elżbieta Wojtowicz, Renata Zawirska-Wojtasiak. Phenolic compounds reduce formation of Nε-(carboxymethyl)lysine and pyrazines formed by Maillard reactions in a model bread system.
Food chemistry.
2017 Sep; 231(?):175-184. doi:
10.1016/j.foodchem.2017.03.126. [PMID: 28449994] - Antonio Dario Troise, Daniele Vitiello, Catherine Tsang, Alberto Fiore. Encapsulation of ascorbic acid promotes the reduction of Maillard reaction products in UHT milk.
Food & function.
2016 Jun; 7(6):2591-602. doi:
10.1039/c6fo00151c. [PMID: 27240727] - Poornima Gopal, Niki L Reynaert, Jean L J M Scheijen, Lean Engelen, Casper G Schalkwijk, Frits M E Franssen, Emiel F M Wouters, Erica P A Rutten. Plasma advanced glycation end-products and skin autofluorescence are increased in COPD.
The European respiratory journal.
2014 Feb; 43(2):430-8. doi:
10.1183/09031936.00135312. [PMID: 23645408] - Nordin M J Hanssen, Lian Engelen, Isabel Ferreira, Jean L J M Scheijen, Maya S Huijberts, Marleen M J van Greevenbroek, Carla J H van der Kallen, Jacqueline M Dekker, Giel Nijpels, Coen D A Stehouwer, Casper G Schalkwijk. Plasma levels of advanced glycation endproducts Nε-(carboxymethyl)lysine, Nε-(carboxyethyl)lysine, and pentosidine are not independently associated with cardiovascular disease in individuals with or without type 2 diabetes: the Hoorn and CODAM studies.
The Journal of clinical endocrinology and metabolism.
2013 Aug; 98(8):E1369-73. doi:
10.1210/jc.2013-1068. [PMID: 23780372] - Yi-Chieh Li, Yi-Min Shih, Jen-Ai Lee. Gentamicin caused renal injury deeply related to methylglyoxal and N(ɛ)-(carboxyethyl)lysine (CEL).
Toxicology letters.
2013 May; 219(1):85-92. doi:
10.1016/j.toxlet.2013.01.024. [PMID: 23454834] - Michael Éverton Andrades, Rodrigo Lorenzi, Ryoji Nagai, José Cláudio Fonseca Moreira, Cristiane Ritter, Felipe Dal-Pizzol. Plasma glycation levels are associated with severity in sepsis.
European journal of clinical investigation.
2012 Oct; 42(10):1055-60. doi:
10.1111/j.1365-2362.2012.02694.x. [PMID: 22625221] - Jinzhou Zhu, Ke Yang, Yajun Jing, Run Du, Zhenbin Zhu, Lin Lu, Ruiyan Zhang. The effects of low-dose nepsilon-(carboxymethyl)lysine (CML) and nepsilon-(carboxyethyl)lysine (CEL), two main glycation free adducts considered as potential uremic toxins, on endothelial progenitor cell function.
Cardiovascular diabetology.
2012 Aug; 11(?):90. doi:
10.1186/1475-2840-11-90. [PMID: 22853433] - Lian Engelen, Frederik Persson, Isabel Ferreira, Peter Rossing, Peter Hovind, Tom Teerlink, Coen D Stehouwer, Hans-Henrik Parving, Casper G Schalkwijk. Irbesartan treatment does not influence plasma levels of the advanced glycation end products N(epsilon)(1-carboxymethyl)lysine and N(epsilon)(1-carboxyethyl)lysine in patients with type 2 diabetes and microalbuminuria. A randomized controlled trial.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2011 Nov; 26(11):3573-7. doi:
10.1093/ndt/gfr102. [PMID: 21385863] - Katsumi Mera, Ryoji Nagai, Kazuhiro Takeo, Miyoko Izumi, Toru Maruyama, Masaki Otagiri. An autoantibody against N(ε)-(carboxyethyl)lysine (CEL): possible involvement in the removal of CEL-modified proteins by macrophages.
Biochemical and biophysical research communications.
2011 Apr; 407(2):420-5. doi:
10.1016/j.bbrc.2011.03.040. [PMID: 21402053] - Trijntje T Cnossen, Ulrich Gladziwa, Jos J van de Kerkhof, Casper G Schalkwijk, Jean Scheijen, Jolanda van Amersfoort, Karin Moret, Charles H Beerenhout, Jeroen P Kooman. The influence of bicarbonate/lactate-buffered PD fluids on N{ε}-(carboxyethyl)lysine and N{ε}-(carboxymethyl)lysine in peritoneal effluent.
Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis.
2011 Mar; 31(2):189-93. doi:
10.3747/pdi.2010.00009. [PMID: 20671103] - Erfan Nur, Dees P Brandjes, John-John B Schnog, Hans-Martin Otten, Karin Fijnvandraat, Casper G Schalkwijk, Bart J Biemond. Plasma levels of advanced glycation end products are associated with haemolysis-related organ complications in sickle cell patients.
British journal of haematology.
2010 Oct; 151(1):62-9. doi:
10.1111/j.1365-2141.2010.08320.x. [PMID: 20678158] - Katrien H J Gaens, Isabel Ferreira, Carla J H van der Kallen, Marleen M J van Greevenbroek, Ellen E Blaak, Edith J M Feskens, Jacqueline M Dekker, Giel Nijpels, Robert J Heine, Leen M 't Hart, Philip G de Groot, Coen D A Stehouwer, Casper G Schalkwijk. Association of polymorphism in the receptor for advanced glycation end products (RAGE) gene with circulating RAGE levels.
The Journal of clinical endocrinology and metabolism.
2009 Dec; 94(12):5174-80. doi:
10.1210/jc.2009-1067. [PMID: 19890027] - Marcus Baumann, Tom Richart, Daniel Sollinger, Jaroslav Pelisek, Marcel Roos, Tatiana Kouznetsova, Hans-Henning Eckstein, Uwe Heemann, Jan A Staessen. Association between carotid diameter and the advanced glycation end product N-epsilon-carboxymethyllysine (CML).
Cardiovascular diabetology.
2009 Aug; 8(?):45. doi:
10.1186/1475-2840-8-45. [PMID: 19660101] - Yeong-Gon Choi, Sabina Lim. Characterization of anti-advanced glycation end product antibodies to nonenzymatically lysine-derived and arginine-derived glycated products.
Journal of immunoassay & immunochemistry.
2009; 30(4):386-99. doi:
10.1080/15321810903188136. [PMID: 19739013] - H L Nienhuis, K de Leeuw, J Bijzet, A Smit, C G Schalkwijk, R Graaff, C G Kallenberg, M Bijl. Skin autofluorescence is increased in systemic lupus erythematosus but is not reflected by elevated plasma levels of advanced glycation endproducts.
Rheumatology (Oxford, England).
2008 Oct; 47(10):1554-8. doi:
10.1093/rheumatology/ken302. [PMID: 18701539] - Jasper W L Hartog, Adriaan A Voors, Casper G Schalkwijk, Jean Scheijen, Tom D J Smilde, Kevin Damman, Stephan J L Bakker, Andries J Smit, Dirk J van Veldhuisen. Clinical and prognostic value of advanced glycation end-products in chronic heart failure.
European heart journal.
2007 Dec; 28(23):2879-85. doi:
10.1093/eurheartj/ehm486. [PMID: 17986469] - N C den Hollander, D J Mulder, R Graaff, S R Thorpe, J W Baynes, G P A Smit, A J Smit. Advanced glycation end products and the absence of premature atherosclerosis in glycogen storage disease Ia.
Journal of inherited metabolic disease.
2007 Nov; 30(6):916-23. doi:
10.1007/s10545-007-0507-0. [PMID: 17570077] - Constantijn J Konings, Casper G Schalkwijk, Frank M van der Sande, Karel M Leunissen, Jeroen P Kooman. Influence of icodextrin on plasma and dialysate levels of N(epsilon)-(carboxymethyl)lysine and N(epsilon)-(carboxyethyl)lysine.
Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis.
2005 Nov; 25(6):591-5. doi:
10.1177/089686080502500616. [PMID: 16411527] - Robert Petrovic, Ján Futas, Ján Chandoga, Vladimír Jakus. Rapid and simple method for determination of Nepsilon-(carboxymethyl)lysine and Nepsilon-(carboxyethyl)lysine in urine using gas chromatography/mass spectrometry.
Biomedical chromatography : BMC.
2005 Nov; 19(9):649-54. doi:
10.1002/bmc.491. [PMID: 15803449] - Miranda T Schram, Casper G Schalkwijk, Aart H Bootsma, John H Fuller, Nish Chaturvedi, Coen D A Stehouwer. Advanced glycation end products are associated with pulse pressure in type 1 diabetes: the EURODIAB Prospective Complications Study.
Hypertension (Dallas, Tex. : 1979).
2005 Jul; 46(1):232-7. doi:
10.1161/01.hyp.0000164574.60279.ba. [PMID: 15851628] - S Agalou, N Ahmed, P J Thornalley, A Dawnay. Advanced glycation end product free adducts are cleared by dialysis.
Annals of the New York Academy of Sciences.
2005 Jun; 1043(?):734-9. doi:
10.1196/annals.1333.085. [PMID: 16037300] - Naila Ahmed, Paul J Thornalley. Peptide mapping of human serum albumin modified minimally by methylglyoxal in vitro and in vivo.
Annals of the New York Academy of Sciences.
2005 Jun; 1043(?):260-6. doi:
10.1196/annals.1333.031. [PMID: 16037246] - Naila Ahmed, Darin Dobler, Mark Dean, Paul J Thornalley. Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity.
The Journal of biological chemistry.
2005 Feb; 280(7):5724-32. doi:
10.1074/jbc.m410973200. [PMID: 15557329] - Wakako Koito, Tomohiro Araki, Seikoh Horiuchi, Ryoji Nagai. Conventional antibody against Nepsilon-(carboxymethyl)lysine (CML) shows cross-reaction to Nepsilon-(carboxyethyl)lysine (CEL): immunochemical quantification of CML with a specific antibody.
Journal of biochemistry.
2004 Dec; 136(6):831-7. doi:
10.1093/jb/mvh193. [PMID: 15671494] - B O Boehm, S Schilling, S Rosinger, G E Lang, G K Lang, R Kientsch-Engel, P Stahl. Elevated serum levels of N(epsilon)-carboxymethyl-lysine, an advanced glycation end product, are associated with proliferative diabetic retinopathy and macular oedema.
Diabetologia.
2004 Aug; 47(8):1376-9. doi:
10.1007/s00125-004-1455-y. [PMID: 15258735] - Tom Teerlink, Rob Barto, Herman J Ten Brink, Casper G Schalkwijk. Measurement of Nepsilon-(carboxymethyl)lysine and Nepsilon-(carboxyethyl)lysine in human plasma protein by stable-isotope-dilution tandem mass spectrometry.
Clinical chemistry.
2004 Jul; 50(7):1222-8. doi:
10.1373/clinchem.2004.031286. [PMID: 15131022] - John W Baynes. The clinical chemome: a tool for the diagnosis and management of chronic disease.
Clinical chemistry.
2004 Jul; 50(7):1116-7. doi:
10.1373/clinchem.2004.034645. [PMID: 15229147] - Jos van de Kerkhof, Casper G Schalkwijk, Constantijn J Konings, Emile C Cheriex, Frank M van der Sande, Peter G Scheffer, Piet M ter Wee, Karel M Leunissen, Jeroen P Kooman. Nepsilon-(carboxymethyl)lysine, Nepsilon-(carboxyethyl)lysine and vascular cell adhesion molecule-1 (VCAM-1) in relation to peritoneal glucose prescription and residual renal function; a study in peritoneal dialysis patients.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2004 Apr; 19(4):910-6. doi:
10.1093/ndt/gfh004. [PMID: 15031349] - Mariska L M Lieuw-A-Fa, Victor W M van Hinsbergh, Tom Teerlink, Rob Barto, Jos Twisk, Coen D A Stehouwer, Casper G Schalkwijk. Increased levels of N(epsilon)-(carboxymethyl)lysine and N(epsilon)-(carboxyethyl)lysine in type 1 diabetic patients with impaired renal function: correlation with markers of endothelial dysfunction.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2004 Mar; 19(3):631-6. doi:
10.1093/ndt/gfg619. [PMID: 14767019] - S Agalou, N Ahmed, A Dawnay, P J Thornalley. Removal of advanced glycation end products in clinical renal failure by peritoneal dialysis and haemodialysis.
Biochemical Society transactions.
2003 Dec; 31(Pt 6):1394-6. doi:
10.1042/bst0311394. [PMID: 14641071] - Ryoji Nagai, Tomohiro Araki, Cristina Miki Hayashi, Fumitaka Hayase, Seikoh Horiuchi. Identification of N epsilon-(carboxyethyl)lysine, one of the methylglyoxal-derived AGE structures, in glucose-modified protein: mechanism for protein modification by reactive aldehydes.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2003 May; 788(1):75-84. doi:
10.1016/s1570-0232(02)01019-x. [PMID: 12668073] - Naila Ahmed, Paul J Thornalley. Chromatographic assay of glycation adducts in human serum albumin glycated in vitro by derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and intrinsic fluorescence.
The Biochemical journal.
2002 May; 364(Pt 1):15-24. doi:
10.1042/bj3640015. [PMID: 11988071] - Naila Ahmed, Ognian K Argirov, Harjit S Minhas, Carlos A A Cordeiro, Paul J Thornalley. Assay of advanced glycation endproducts (AGEs): surveying AGEs by chromatographic assay with derivatization by 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and application to Nepsilon-carboxymethyl-lysine- and Nepsilon-(1-carboxyethyl)lysine-modified albumin.
The Biochemical journal.
2002 May; 364(Pt 1):1-14. doi:
10.1042/bj3640001. [PMID: 11988070] - M U Ahmed, E Brinkmann Frye, T P Degenhardt, S R Thorpe, J W Baynes. N-epsilon-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins.
The Biochemical journal.
1997 Jun; 324 ( Pt 2)(?):565-70. doi:
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