O-Sulfotyrosine (BioDeep_00000117135)

   

human metabolite blood metabolite


代谢物信息卡片


(2S)-2-Amino-3-[4-(sulphooxy)phenyl]propanoic acid

化学式: C9H11NO6S (261.0307)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 10.21%

分子结构信息

SMILES: C1=CC(=CC=C1CC(C(=O)O)N)OS(=O)(=O)O
InChI: InChI=1S/C9H11NO6S/c10-8(9(11)12)5-6-1-3-7(4-2-6)16-17(13,14)15/h1-4,8H,5,10H2,(H,11,12)(H,13,14,15)/t8-/m0/s1

描述信息

O-Sulfotyrosine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from a reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. O-Sulfotyrosine has been identified as a potential plasma biomarker of reduced kidney function in early chronic kidney disease (CKD), end stage renal disease (ESRD), and hemodialytic clearance (PMID: 31048706). Human plasma levels of O-sulfotyrosine were reported to be influenced by genetic variants in the gene ARSA which codes for the enzyme arylsulfatase A (PMID: 24816252).

同义名列表

28 个代谢物同义名

(2S)-2-Amino-3-[4-(sulphooxy)phenyl]propanoic acid; (2S)-2-Amino-3-[4-(sulfooxy)phenyl]propanoic acid; (2S)-2-Azanyl-3-(4-sulphooxyphenyl)propanoic acid; (2S)-2-Azanyl-3-(4-sulfooxyphenyl)propanoic acid; (2S)-2-Amino-3-[4-(sulphooxy)phenyl]propanoate; (2S)-2-Amino-3-[4-(sulfooxy)phenyl]propanoate; (2S)-2-Azanyl-3-(4-sulphooxyphenyl)propanoate; (2S)-2-Azanyl-3-(4-sulfooxyphenyl)propanoate; L-Tyrosine O-sulphuric acid; L-Tyrosine O-sulfuric acid; Tyrosine O-sulphuric acid; Tyrosine O-sulfuric acid; Tyrosine sulphuric acid; O(4)-SulphO-L-tyrosine; Tyrosine sulfuric acid; L-Tyrosine O-sulphate; L-Tyrosine O-sulfate; Tyrosine O-sulphate; O-SulphO-L-tyrosine; O-SulfO-L-tyrosine; Tyrosine O-sulfate; Tyrosine sulphate; Tyrosine sulfate; O-Sulphotyrosine; O-Sulfotyrosine; Sulphotyrosine; O-Decasulfate; Sulfotyrosine



数据库引用编号

7 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)

1 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。

亚细胞结构定位 关联基因列表


文献列表

  • Valley Stewart, Pamela C Ronald. Sulfotyrosine residues: Interaction specificity determinants for extracellular protein-protein interactions. The Journal of biological chemistry. 2022 08; 298(8):102232. doi: 10.1016/j.jbc.2022.102232. [PMID: 35798140]
  • Shuai Chen, Yong-Hua Liu, Dao-Peng Dai, Zheng-Bin Zhu, Yang Dai, Zhi-Ming Wu, Li-Ping Zhang, Zhi-Feng Duan, Lin Lu, Feng-Hua Ding, Jin-Zhou Zhu, Rui-Yan Zhang. Using circulating O-sulfotyrosine in the differential diagnosis of acute kidney injury and chronic kidney disease. BMC nephrology. 2021 02; 22(1):66. doi: 10.1186/s12882-021-02268-3. [PMID: 33622294]
  • Justin T H Chan, Yanling Liu, Srijit Khan, Jonathan R St-Germain, Chunxia Zou, Leslie Y T Leung, Judi Yang, Mengyao Shi, Eyal Grunebaum, Paolo Campisi, Evan J Propst, Theresa Holler, Amit Bar-Or, Joan E Wither, Christopher W Cairo, Michael F Moran, Alexander F Palazzo, Max D Cooper, Götz R A Ehrhardt. A tyrosine sulfation-dependent HLA-I modification identifies memory B cells and plasma cells. Science advances. 2018 11; 4(11):eaar7653. doi: 10.1126/sciadv.aar7653. [PMID: 30417091]
  • Benjamin Schwessinger, Xiang Li, Thomas L Ellinghaus, Leanne Jade G Chan, Tong Wei, Anna Joe, Nicholas Thomas, Rory Pruitt, Paul D Adams, Maw Sheng Chern, Christopher J Petzold, Chang C Liu, Pamela C Ronald. A second-generation expression system for tyrosine-sulfated proteins and its application in crop protection. Integrative biology : quantitative biosciences from nano to macro. 2016 Apr; 8(4):542-5. doi: 10.1039/c5ib00232j. [PMID: 26611838]
  • Cajetan Dogo-Isonagie, Su-Lin Lee, Katheryn Lohith, Hongbing Liu, Sivakoteswara R Mandadapu, Sabrina Lusvarghi, Robert D O'Connor, Carole A Bewley. Design and synthesis of small molecule-sulfotyrosine mimetics that inhibit HIV-1 entry. Bioorganic & medicinal chemistry. 2016 Apr; 24(8):1718-28. doi: 10.1016/j.bmc.2016.02.044. [PMID: 26968647]
  • Yunping Shen, Andrew C Diener. Arabidopsis thaliana resistance to fusarium oxysporum 2 implicates tyrosine-sulfated peptide signaling in susceptibility and resistance to root infection. PLoS genetics. 2013 May; 9(5):e1003525. doi: 10.1371/journal.pgen.1003525. [PMID: 23717215]
  • A Gringeri, F A Ofosu, S Grancha, J Oldenburg, N P Ewing, A B Federici. Understanding FVIII/VWF complex--report from a symposium of XXIX WFH meeting 2010. Haemophilia : the official journal of the World Federation of Hemophilia. 2012 May; 18(3):469-75. doi: 10.1111/j.1365-2516.2011.02655.x. [PMID: 21943193]
  • Stephan Wawra, Judith Bain, Elaine Durward, Irene de Bruijn, Kirsty L Minor, Anja Matena, Lars Löbach, Stephen C Whisson, Peter Bayer, Andrew J Porter, Paul R J Birch, Chris J Secombes, Pieter van West. Host-targeting protein 1 (SpHtp1) from the oomycete Saprolegnia parasitica translocates specifically into fish cells in a tyrosine-O-sulphate-dependent manner. Proceedings of the National Academy of Sciences of the United States of America. 2012 Feb; 109(6):2096-101. doi: 10.1073/pnas.1113775109. [PMID: 22308362]
  • Yara Banz, Otto M Hess, Pascal Meier, Elena Y Korchagina, Elena A Gordeeva, Simon C Robson, Thusitha Gajanayake, Eva Csizmadia, Daniel Mettler, André Haeberli, Nicolai V Bovin, Robert Rieben. Evaluation of multimeric tyrosine-O-sulfate as a cytoprotectant in an in vivo model of acute myocardial infarction in pigs. Cardiology. 2012; 121(1):59-70. doi: 10.1159/000336485. [PMID: 22398380]
  • Jong-Seo Kim, Si-Uk Song, Hie-Joon Kim. Simultaneous identification of tyrosine phosphorylation and sulfation sites utilizing tyrosine-specific bromination. Journal of the American Society for Mass Spectrometry. 2011 Nov; 22(11):1916-25. doi: 10.1007/s13361-011-0214-9. [PMID: 21952757]
  • Yoshikatsu Matsubayashi. Post-translational modifications in secreted peptide hormones in plants. Plant & cell physiology. 2011 Jan; 52(1):5-13. doi: 10.1093/pcp/pcq169. [PMID: 21071428]
  • Claudia Sa E Cunha, Natalie J Griffiths, Mumtaz Virji. Neisseria meningitidis Opc invasin binds to the sulphated tyrosines of activated vitronectin to attach to and invade human brain endothelial cells. PLoS pathogens. 2010 May; 6(5):e1000911. doi: 10.1371/journal.ppat.1000911. [PMID: 20502634]
  • Scott A Young, Samir Julka, Glenn Bartley, Jeffrey R Gilbert, Brian M Wendelburg, Shao-Ching Hung, W H Kerr Anderson, Wallace H Yokoyama. Quantification of the sulfated cholecystokinin CCK-8 in hamster plasma using immunoprecipitation liquid chromatography-mass spectrometry/mass spectrometry. Analytical chemistry. 2009 Nov; 81(21):9120-8. doi: 10.1021/ac9018318. [PMID: 19799376]
  • Son N Lam, Priyamvada Acharya, Richard Wyatt, Peter D Kwong, Carole A Bewley. Tyrosine-sulfate isosteres of CCR5 N-terminus as tools for studying HIV-1 entry. Bioorganic & medicinal chemistry. 2008 Dec; 16(23):10113-20. doi: 10.1016/j.bmc.2008.10.005. [PMID: 18952441]
  • Caroline Tauxe, Xun Xie, Magali Joffraud, Manuel Martinez, Marc Schapira, Olivier Spertini. P-selectin glycoprotein ligand-1 decameric repeats regulate selectin-dependent rolling under flow conditions. The Journal of biological chemistry. 2008 Oct; 283(42):28536-45. doi: 10.1074/jbc.m802865200. [PMID: 18713749]
  • Chon-Ho Yen, Chi-Kai Yang, I-Chung Chen, Yin-Shen Lin, Chih-Sheng Lin, Sen Chu, Ching-Fu Tu. Expression of recombinant Hirudin in transgenic mice milk driven by the goat beta-casein promoter. Biotechnology journal. 2008 Aug; 3(8):1067-77. doi: 10.1002/biot.200800069. [PMID: 18543243]
  • Jin-Ming Gao, Qi-Ping Feng, Jin Zuo, Fu-De Fang, Lei Jiang, Zi-Jian Guo. [Regulation of tyrosylprotein sulfotransferases activity by sulfotyrosine]. Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae. 2007 Apr; 29(2):241-5. doi: NULL. [PMID: 17536277]
  • Miklós Sahin-Tóth, Zoltán Kukor, Zsófia Nemoda. Human cationic trypsinogen is sulfated on Tyr154. The FEBS journal. 2006 Nov; 273(22):5044-50. doi: 10.1111/j.1742-4658.2006.05501.x. [PMID: 17087724]
  • Clifford Lingwood, Murugesapillai Mylvaganam, Farah Minhas, Beth Binnington, Donald R Branch, Régis Pomès. The sulfogalactose moiety of sulfoglycosphingolipids serves as a mimic of tyrosine phosphate in many recognition processes. Prediction and demonstration of Src homology 2 domain/sulfogalactose binding. The Journal of biological chemistry. 2005 Apr; 280(13):12542-7. doi: 10.1074/jbc.m413724200. [PMID: 15634687]
  • Mogjiborahman Salek, Sabine Costagliola, Wolf D Lehmann. Protein tyrosine-O-sulfation analysis by exhaustive product ion scanning with minimum collision offset in a NanoESI Q-TOF tandem mass spectrometer. Analytical chemistry. 2004 Sep; 76(17):5136-42. doi: 10.1021/ac0400414. [PMID: 15373453]
  • Thomas Laumonier, Alexander J Walpen, Katja M Matozan, Elena Y Korchagina, Nicolai V Bovin, André Haeberli, Paul J Mohacsi, Robert Rieben. Multimeric tyrosine sulfate acts as an endothelial cell protectant and prevents complement activation in xenotransplantation models. Xenotransplantation. 2004 May; 11(3):262-8. doi: 10.1111/j.1399-3089.2004.00125.x. [PMID: 15099206]
  • Patrik Onnerfjord, Terrence F Heathfield, Dick Heinegård. Identification of tyrosine sulfation in extracellular leucine-rich repeat proteins using mass spectrometry. The Journal of biological chemistry. 2004 Jan; 279(1):26-33. doi: 10.1074/jbc.m308689200. [PMID: 14551184]
  • Jennifer W Mitchell, Frank C Church. Aspartic acid residues 72 and 75 and tyrosine-sulfate 73 of heparin cofactor II promote intramolecular interactions during glycosaminoglycan binding and thrombin inhibition. The Journal of biological chemistry. 2002 May; 277(22):19823-30. doi: 10.1074/jbc.m200630200. [PMID: 11856753]
  • Christine Galustian, Robert A Childs, Mark Stoll, Hideharu Ishida, Makoto Kiso, Ten Feizi. Synergistic interactions of the two classes of ligand, sialyl-Lewis(a/x) fuco-oligosaccharides and short sulpho-motifs, with the P- and L-selectins: implications for therapeutic inhibitor designs. Immunology. 2002 Mar; 105(3):350-9. doi: 10.1046/j.1365-2567.2002.01369.x. [PMID: 11918697]
  • J C Severs, M Carnine, H Eguizabal, K K Mock. Characterization of tyrosine sulfate residues in antihemophilic recombinant factor VIII by liquid chromatography electrospray ionization tandem mass spectrometry and amino acid analysis. Rapid communications in mass spectrometry : RCM. 1999; 13(11):1016-23. doi: 10.1002/(sici)1097-0231(19990615)13:11<1016::aid-rcm599>3.0.co;2-5. [PMID: 10368977]
  • J G Ranasinghe, Y Sakakibara, M Harada, K Nishiyama, M C Liu, M Suiko. Structural identification of sulfated tyrosine in human urine. Bioscience, biotechnology, and biochemistry. 1999 Jan; 63(1):229-31. doi: 10.1271/bbb.63.229. [PMID: 10052149]
  • J F Rehfeld. Accurate measurement of cholecystokinin in plasma. Clinical chemistry. 1998 May; 44(5):991-1001. doi: 10.1093/clinchem/44.5.991. [PMID: 9590372]
  • M Kjalke, A Heding, G Talbo, E Persson, J Thomsen, M Ezban. Amino acid residues 721-729 are required for full factor VIII activity. European journal of biochemistry. 1995 Dec; 234(3):773-9. doi: 10.1111/j.1432-1033.1995.773_a.x. [PMID: 8575434]
  • B Leitinger, J L Brown, M Spiess. Tagging secretory and membrane proteins with a tyrosine sulfation site. Tyrosine sulfation precedes galactosylation and sialylation in COS-7 cells. The Journal of biological chemistry. 1994 Mar; 269(11):8115-21. doi: 10.1016/s0021-9258(17)37167-3. [PMID: 8132536]
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  • M Suiko, P H Fernando, Y Arino, M Terada, S Nakatsu, M C Liu. Quantitation of tyrosine-O-sulfate in human urine by ion-pair reverse-phase high-performance liquid chromatography. Clinica chimica acta; international journal of clinical chemistry. 1990 Dec; 193(3):193-7. doi: 10.1016/0009-8981(90)90251-m. [PMID: 2282697]
  • G Hortin, D M Tollefsen, A W Strauss. Identification of two sites of sulfation of human heparin cofactor II. The Journal of biological chemistry. 1986 Dec; 261(34):15827-30. doi: NULL. [PMID: 3782093]
  • S Fukui, Y Numata, I Yamashina. Comparison of protein sulfation in control and virus-transformed baby hamster kidney cells. Journal of biochemistry. 1984 Dec; 96(6):1783-8. doi: 10.1093/oxfordjournals.jbchem.a135011. [PMID: 6099354]
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