fructosyl-lysine (BioDeep_00000898096)

Main id: BioDeep_00000034722

 

PANOMIX_OTCML-2023


代谢物信息卡片


fructosyl-lysine

化学式: C12H24N2O7 (308.1583434)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(CCNCC(=O)C(C(C(CO)O)O)O)CC(C(=O)O)N
InChI: InChI=1S/C12H24N2O7/c13-7(12(20)21)3-1-2-4-14-5-8(16)10(18)11(19)9(17)6-15/h7,9-11,14-15,17-19H,1-6,13H2,(H,20,21)/t7-,9+,10+,11+/m0/s1

描述信息

Fructosyl-lysine (Fructoselysine) is an amadori glycation product from the reaction of glucose and lysine by the Maillard reaction. Fructosyl-lysine is the precursor to glucosepane, a lysine–arginine protein cross-link that can be an indicator in diabetes?detection[1].

同义名列表

2 个代谢物同义名

fructosyl-lysine; Fructoselysine



数据库引用编号

4 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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)

0 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

  • Katja C W van Dongen, Meike van der Zande, Ben Bruyneel, Jacques J M Vervoort, Ivonne M C M Rietjens, Clara Belzer, Karsten Beekmann. An in vitro model for microbial fructoselysine degradation shows substantial interindividual differences in metabolic capacities of human fecal slurries. Toxicology in vitro : an international journal published in association with BIBRA. 2021 Apr; 72(?):105078. doi: 10.1016/j.tiv.2021.105078. [PMID: 33429044]
  • Ye Jiao, Jialiang He, Zhiyong He, Daming Gao, Fang Qin, Mingyong Xie, Maomao Zeng, Jie Chen. Formation of Nε-(carboxymethyl)lysine and Nε-(carboxyethyl)lysine during black tea processing. Food research international (Ottawa, Ont.). 2019 07; 121(?):738-745. doi: 10.1016/j.foodres.2018.12.051. [PMID: 31108804]
  • Urszula Razny, Joanna Goralska, Anna Zdzienicka, Danuta Fedak, Jinit Masania, Naila Rabbani, Paul Thornalley, Dorota Pawlica-Gosiewska, Katarzyna Gawlik, Aldona Dembinska-Kiec, Bogdan Solnica, Malgorzata Malczewska-Malec. Relation of the protein glycation, oxidation and nitration to the osteocalcin level in obese subjects. Acta biochimica Polonica. 2017; 64(3):415-422. doi: 10.18388/abp.2017_1627. [PMID: 28841723]
  • Lusani Norah Vhangani, Jessy Van Wyk. Antioxidant activity of Maillard reaction products (MRPs) in a lipid-rich model system. Food chemistry. 2016 Oct; 208(?):301-8. doi: 10.1016/j.foodchem.2016.03.100. [PMID: 27132854]
  • C van Rooijen, G Bosch, C I Butré, A F B van der Poel, P A Wierenga, L Alexander, W H Hendriks. Urinary excretion of dietary Maillard reaction products in healthy adult female cats. Journal of animal science. 2016 Jan; 94(1):185-95. doi: 10.2527/jas.2015-9550. [PMID: 26812325]
  • Thi Phuong Nam Bui, Jarmo Ritari, Sjef Boeren, Pieter de Waard, Caroline M Plugge, Willem M de Vos. Production of butyrate from lysine and the Amadori product fructoselysine by a human gut commensal. Nature communications. 2015 Dec; 6(?):10062. doi: 10.1038/ncomms10062. [PMID: 26620920]
  • Joshua I Barzilay, Kathleen A Jablonski, Vivian Fonseca, Steven E Shoelson, Allison B Goldfine, Christopher Strauch, Vincent M Monnier. The impact of salsalate treatment on serum levels of advanced glycation end products in type 2 diabetes. Diabetes care. 2014 Apr; 37(4):1083-91. doi: 10.2337/dc13-1527. [PMID: 24255104]
  • Lipeng Han, Lin Li, Bing Li, Di Zhao, Yuting Li, Zhenbo Xu, Guoqin Liu. Hydroxyl radical induced by lipid in Maillard reaction model system promotes diet-derived N(ε)-carboxymethyllysine formation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Oct; 60(?):536-41. doi: 10.1016/j.fct.2013.07.081. [PMID: 23959106]
  • Bruce A Perkins, Naila Rabbani, Andrew Weston, Linda H Ficociello, Antonysunil Adaikalakoteswari, Monika Niewczas, James Warram, Andrzej S Krolewski, Paul Thornalley. Serum levels of advanced glycation endproducts and other markers of protein damage in early diabetic nephropathy in type 1 diabetes. PloS one. 2012; 7(4):e35655. doi: 10.1371/journal.pone.0035655. [PMID: 22558190]
  • Omar S Barnaby, Ronald L Cerny, William Clarke, David S Hage. Quantitative analysis of glycation patterns in human serum albumin using 16O/18O-labeling and MALDI-TOF MS. Clinica chimica acta; international journal of clinical chemistry. 2011 Aug; 412(17-18):1606-15. doi: 10.1016/j.cca.2011.05.012. [PMID: 21601565]
  • Nasser Zangiabadi, Majid Asadi-Shekaari, Vahid Sheibani, Mandana Jafari, Mohammad Shabani, Ali Reza Asadi, Hale Tajadini, Morteza Jarahi. Date fruit extract is a neuroprotective agent in diabetic peripheral neuropathy in streptozotocin-induced diabetic rats: a multimodal analysis. Oxidative medicine and cellular longevity. 2011; 2011(?):976948. doi: 10.1155/2011/976948. [PMID: 22191015]
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  • Anusooya S Sivam, Dongxiao Sun-Waterhouse, SiewYoung Quek, Conrad O Perera. Properties of bread dough with added fiber polysaccharides and phenolic antioxidants: a review. Journal of food science. 2010 Oct; 75(8):R163-74. doi: 10.1111/j.1750-3841.2010.01815.x. [PMID: 21535512]
  • Omar S Barnaby, Chunling Wa, Ronald L Cerny, William Clarke, David S Hage. Quantitative analysis of glycation sites on human serum albumin using (16)O/(18)O-labeling and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Clinica chimica acta; international journal of clinical chemistry. 2010 Aug; 411(15-16):1102-10. doi: 10.1016/j.cca.2010.04.007. [PMID: 20394739]
  • N Karachalias, R Babaei-Jadidi, N Rabbani, P J Thornalley. Increased protein damage in renal glomeruli, retina, nerve, plasma and urine and its prevention by thiamine and benfotiamine therapy in a rat model of diabetes. Diabetologia. 2010 Jul; 53(7):1506-16. doi: 10.1007/s00125-010-1722-z. [PMID: 20369223]
  • Juliette Fortpied, Didier Vertommen, Emile Van Schaftingen. Binding of mannose-binding lectin to fructosamines: a potential link between hyperglycaemia and complement activation in diabetes. Diabetes/metabolism research and reviews. 2010 May; 26(4):254-60. doi: 10.1002/dmrr.1079. [PMID: 20503257]
  • Naila Rabbani, Madhu Varma Chittari, Charles W Bodmer, Daniel Zehnder, Antonio Ceriello, Paul J Thornalley. Increased glycation and oxidative damage to apolipoprotein B100 of LDL cholesterol in patients with type 2 diabetes and effect of metformin. Diabetes. 2010 Apr; 59(4):1038-45. doi: 10.2337/db09-1455. [PMID: 20068133]
  • Markus A Queisser, Dachun Yao, Sven Geisler, Hans-Peter Hammes, Günter Lochnit, Erwin D Schleicher, Michael Brownlee, Klaus T Preissner. Hyperglycemia impairs proteasome function by methylglyoxal. Diabetes. 2010 Mar; 59(3):670-8. doi: 10.2337/db08-1565. [PMID: 20009088]
  • Justin A MacDonald, Thorsten Degenhardt, John W Baynes, Kenneth B Storey. Glycation of wood frog (Rana sylvatica) hemoglobin and blood proteins: in vivo and in vitro studies. Cryobiology. 2009 Oct; 59(2):223-5. doi: 10.1016/j.cryobiol.2009.06.008. [PMID: 19540217]
  • Jiaqian Ni, Xianglin Yuan, Jiayin Gu, Xiuzhen Yue, Xiaorong Gu, Ram H Nagaraj, John W Crabb. Plasma protein pentosidine and carboxymethyllysine, biomarkers for age-related macular degeneration. Molecular & cellular proteomics : MCP. 2009 Aug; 8(8):1921-33. doi: 10.1074/mcp.m900127-mcp200. [PMID: 19435712]
  • Katarĺna Sebeková, Veronika Somoza, Monika Jarcusková, August Heidland, Ludmila Podracká. Plasma advanced glycation end products are decreased in obese children compared with lean controls. International journal of pediatric obesity : IJPO : an official journal of the International Association for the Study of Obesity. 2009; 4(2):112-8. doi: 10.1080/17477160802248039. [PMID: 18645732]
  • T Lauer, T Rassaf, C Planitz, R Preuss, R Krause, T Henle, A Deussen. Evidence against nitric oxide-quenching effects of chemically defined Maillard reaction products. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2008 Apr; 40(4):233-8. doi: 10.1055/s-2008-1058062. [PMID: 18548382]
  • Chunling Wa, Ronald L Cerny, William A Clarke, David S Hage. Characterization of glycation adducts on human serum albumin by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Clinica chimica acta; international journal of clinical chemistry. 2007 Oct; 385(1-2):48-60. doi: 10.1016/j.cca.2007.06.011. [PMID: 17707360]
  • Maki Fujiwara, Jun-ichi Sumitani, Shinji Koga, Issei Yoshioka, Takuji Kouzuma, Shigeyuki Imamura, Takashi Kawaguchi, Motoo Arai. Alteration of substrate specificity of fructosyl-amino acid oxidase from Fusarium oxysporum. Applied microbiology and biotechnology. 2007 Mar; 74(4):813-9. doi: 10.1007/s00253-006-0720-z. [PMID: 17160532]
  • Maria Veiga da-Cunha, Patrick Jacquemin, Ghislain Delpierre, Catherine Godfraind, Ivan Théate, Didier Vertommen, Frédéric Clotman, Frédéric Lemaigre, Olivier Devuyst, Emile Van Schaftingen. Increased protein glycation in fructosamine 3-kinase-deficient mice. The Biochemical journal. 2006 Oct; 399(2):257-64. doi: 10.1042/bj20060684. [PMID: 16819943]
  • Christina Hultsch, Michael Hellwig, Beate Pawelke, Ralf Bergmann, Katrin Rode, Jens Pietzsch, René Krause, Thomas Henle. Biodistribution and catabolism of 18F-labeled N-epsilon-fructoselysine as a model of Amadori products. Nuclear medicine and biology. 2006 Oct; 33(7):865-73. doi: 10.1016/j.nucmedbio.2006.07.007. [PMID: 17045166]
  • Veronika Somoza, Elisabeth Wenzel, Carola Weiss, Ingrid Clawin-Rädecker, Nadine Grübel, Helmut F Erbersdobler. Dose-dependent utilisation of casein-linked lysinoalanine, N(epsilon)-fructoselysine and N(epsilon)-carboxymethyllysine in rats. Molecular nutrition & food research. 2006 Sep; 50(9):833-41. doi: 10.1002/mnfr.200600021. [PMID: 16917812]
  • Sudesh Vasdev, Vicki Gill, Pawan K Singal. Beneficial effect of low ethanol intake on the cardiovascular system: possible biochemical mechanisms. Vascular health and risk management. 2006; 2(3):263-76. doi: 10.2147/vhrm.2006.2.3.263. [PMID: 17326332]
  • Naila Ahmed, Roya Babaei-Jadidi, Scott K Howell, Paul J Thornalley, Paul J Beisswenger. Glycated and oxidized protein degradation products are indicators of fasting and postprandial hyperglycemia in diabetes. Diabetes care. 2005 Oct; 28(10):2465-71. doi: 10.2337/diacare.28.10.2465. [PMID: 16186281]
  • N V Chuyen, H Arai, T Nakanishi, N Utsunomiya. Are food advanced glycation end products toxic in biological systems?. Annals of the New York Academy of Sciences. 2005 Jun; 1043(?):467-73. doi: 10.1196/annals.1333.053. [PMID: 16037268]
  • Naila Ahmed, Paul J Thornalley, Reinhard Lüthen, Dieter Häussinger, Katarina Sebekova, Reinhard Schinzel, Wolfram Voelker, August Heidland. Processing of protein glycation, oxidation and nitrosation adducts in the liver and the effect of cirrhosis. Journal of hepatology. 2004 Dec; 41(6):913-9. doi: 10.1016/j.jhep.2004.08.007. [PMID: 15582123]
  • Nadja Alt, James A Carson, Nathan L Alderson, Yuping Wang, Ryoji Nagai, Thomas Henle, Suzanne R Thorpe, John W Baynes. Chemical modification of muscle protein in diabetes. Archives of biochemistry and biophysics. 2004 May; 425(2):200-6. doi: 10.1016/j.abb.2004.03.012. [PMID: 15111128]
  • N Karachalias, R Babaei-Jadidi, N Ahmed, P J Thornalley. Accumulation of fructosyl-lysine and advanced glycation end products in the kidney, retina and peripheral nerve of streptozotocin-induced diabetic rats. Biochemical Society transactions. 2003 Dec; 31(Pt 6):1423-5. doi: 10.1042/bst0311423. [PMID: 14641079]
  • Paul J Thornalley, Sinan Battah, Naila Ahmed, Nikolaos Karachalias, Stamatina Agalou, Roya Babaei-Jadidi, Anne Dawnay. Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry. The Biochemical journal. 2003 Nov; 375(Pt 3):581-92. doi: 10.1042/bj20030763. [PMID: 12885296]
  • Takashi Nagasawa, Nobuaki Tabata, Yoshiaki Ito, Youichi Aiba, Naoyuki Nishizawa, David D Kitts. Dietary G-rutin suppresses glycation in tissue proteins of streptozotocin-induced diabetic rats. Molecular and cellular biochemistry. 2003 Oct; 252(1-2):141-7. doi: 10.1023/a:1025563519088. [PMID: 14577587]
  • 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]
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  • V Y Wu, C W Shearman, M P Cohen. Identification of calnexin as a binding protein for Amadori-modified glycated albumin. Biochemical and biophysical research communications. 2001 Jun; 284(3):602-6. doi: 10.1006/bbrc.2001.4982. [PMID: 11396943]
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  • M F Weiss, P Erhard, F A Kader-Attia, Y C Wu, P B Deoreo, A Araki, M A Glomb, V M Monnier. Mechanisms for the formation of glycoxidation products in end-stage renal disease. Kidney international. 2000 Jun; 57(6):2571-85. doi: 10.1046/j.1523-1755.2000.00117.x. [PMID: 10844627]
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