L-Methionine (R)-S-oxide (BioDeep_00000838640)

   


代谢物信息卡片


L-Methionine (R)-S-oxide

化学式: C5H11NO3S (165.0459616)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 5.41%

分子结构信息

SMILES: CS(=O)CCC(C(=O)O)N
InChI: InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m0/s1

描述信息

The (R)-oxido diastereomer of L-methionine S-oxide.

同义名列表

1 个代谢物同义名

L-Methionine (R)-S-oxide



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(1)

BioCyc(0)

PlantCyc(0)

代谢反应

24 个相关的代谢反应过程信息。

Reactome(24)

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

  • Ewa Marzena Kalemba, Kris Gevaert, Francis Impens, Sara Dufour, Anna Czerwoniec. The association of protein-bound methionine sulfoxide with proteomic basis for aging in beech seeds. BMC plant biology. 2024 May; 24(1):377. doi: 10.1186/s12870-024-05085-6. [PMID: 38714916]
  • Darren Leahy, Cameron Grant, Alex Jackson, Alex Duff, Nicholas Tardiota, Jessica Van Haeften, Xingchen Chen, Jonathan M Peake, Michael D Kruppa, Eliot T Smith, David A Johnson, William B Lott, Jonathan M Harris. Discrimination of Methionine Sulfoxide and Sulfone by Human Neutrophil Elastase. Molecules (Basel, Switzerland). 2021 Sep; 26(17):. doi: 10.3390/molecules26175344. [PMID: 34500777]
  • Natalia Wojciechowska, Shirin Alipour, Ewelina Stolarska, Karolina Bilska, Pascal Rey, Ewa M Kalemba. Involvement of the MetO/Msr System in Two Acer Species That Display Contrasting Characteristics during Germination. International journal of molecular sciences. 2020 Dec; 21(23):. doi: 10.3390/ijms21239197. [PMID: 33276642]
  • Su H Chu, Jing Cui, Jeffrey A Sparks, Bing Lu, Sara K Tedeschi, Cameron B Speyer, LauraKay Moss, Marie L Feser, Lindsay B Kelmenson, Elizabeth A Mewshaw, Jess D Edison, Kevin D Deane, Clary Clish, Jessica Lasky-Su, Elizabeth W Karlson, Karen H Costenbader. Circulating plasma metabolites and risk of rheumatoid arthritis in the Nurses' Health Study. Rheumatology (Oxford, England). 2020 11; 59(11):3369-3379. doi: 10.1093/rheumatology/keaa125. [PMID: 32310291]
  • Tiffany Thomas, Davide Stefanoni, Julie A Reisz, Travis Nemkov, Lorenzo Bertolone, Richard O Francis, Krystalyn E Hudson, James C Zimring, Kirk C Hansen, Eldad A Hod, Steven L Spitalnik, Angelo D'Alessandro. COVID-19 infection alters kynurenine and fatty acid metabolism, correlating with IL-6 levels and renal status. JCI insight. 2020 07; 5(14):. doi: 10.1172/jci.insight.140327. [PMID: 32559180]
  • Thaís S Franceschi, Mayara S P Soares, Nathalia S Pedra, Natália P Bona, Luiza Spohr, Fernanda C Teixeira, Carlus A T do Couto, Roselia M Spanevello, Marion Deon, Carmen R Vargas, Elizandra Braganhol, Francieli M Stefanello. Characterization of macrophage phenotype, redox, and purinergic response upon chronic treatment with methionine and methionine sulfoxide in mice. Amino acids. 2020 Apr; 52(4):629-638. doi: 10.1007/s00726-020-02841-4. [PMID: 32246211]
  • Kristine B Holte, Mona Svanteson, Kristian F Hanssen, Kari Anne Sveen, Ingebjørg Seljeflot, Svein Solheim, David R Sell, Vincent M Monnier, Tore Julsrud Berg. Collagen methionine sulfoxide and glucuronidine/LW-1 are markers of coronary artery disease in long-term survivors with type 1 diabetes. The Dialong study. PloS one. 2020; 15(5):e0233174. doi: 10.1371/journal.pone.0233174. [PMID: 32401813]
  • Maurizio Bruschi, Andrea Petretto, Laura Santucci, Augusto Vaglio, Federico Pratesi, Paola Migliorini, Roberta Bertelli, Chiara Lavarello, Martina Bartolucci, Giovanni Candiano, Marco Prunotto, Gian Marco Ghiggeri. Neutrophil Extracellular Traps protein composition is specific for patients with Lupus nephritis and includes methyl-oxidized αenolase (methionine sulfoxide 93). Scientific reports. 2019 05; 9(1):7934. doi: 10.1038/s41598-019-44379-w. [PMID: 31138830]
  • Mayara Sandrielly Pereira Soares, Marcelo Zanusso Costa, Tatiane Morgana da Silva, Marta Gazal, Carlus Augustu Tavares do Couto, Gabriela Nogueira Debom, Rodrigo Rodrigues, Juliana Hofstätter Azambuja, Emerson André Casali, Cesar Eduardo Jacintho Moritz, Marta Frescura Duarte, Elizandra Braganhol, Francieli Moro Stefanello, Roselia Maria Spanevello. Methionine and/or Methionine Sulfoxide Alter Ectoenzymes Activities in Lymphocytes and Inflammatory Parameters in Serum from Young Rats: Acute and Chronic Effects. Cell biochemistry and biophysics. 2018 Jun; 76(1-2):243-253. doi: 10.1007/s12013-017-0815-4. [PMID: 28726179]
  • Ákos Kenéz, Tobias Warnken, Karsten Feige, Korinna Huber. Lower plasma trans-4-hydroxyproline and methionine sulfoxide levels are associated with insulin dysregulation in horses. BMC veterinary research. 2018 May; 14(1):146. doi: 10.1186/s12917-018-1479-z. [PMID: 29716602]
  • Juraj Koska, Aramesh Saremi, Scott Howell, Gideon Bahn, Barbora De Courten, Henry Ginsberg, Paul J Beisswenger, Peter D Reaven. Advanced Glycation End Products, Oxidation Products, and Incident Cardiovascular Events in Patients With Type 2 Diabetes. Diabetes care. 2018 03; 41(3):570-576. doi: 10.2337/dc17-1740. [PMID: 29208654]
  • Maria-Armineh Tossounian, Inge Van Molle, Khadija Wahni, Silke Jacques, Kris Gevaert, Frank Van Breusegem, Didier Vertommen, David Young, Leonardo Astolfi Rosado, Joris Messens. Disulfide bond formation protects Arabidopsis thaliana glutathione transferase tau 23 from oxidative damage. Biochimica et biophysica acta. General subjects. 2018 03; 1862(3):775-789. doi: 10.1016/j.bbagen.2017.10.007. [PMID: 29031766]
  • Mayara Sandrielly Pereira Soares, Cassiana Macagnan Viau, Jenifer Saffi, Marcelo Zanusso Costa, Tatiane Morgana da Silva, Pathise Souto Oliveira, Juliana Hofstatter Azambuja, Alethéa Gatto Barschak, Elizandra Braganhol, Angela T S Wyse, Roselia Maria Spanevello, Francieli Moro Stefanello. Acute administration of methionine and/or methionine sulfoxide impairs redox status and induces apoptosis in rat cerebral cortex. Metabolic brain disease. 2017 10; 32(5):1693-1703. doi: 10.1007/s11011-017-0054-9. [PMID: 28676970]
  • Martina I Boxler, Matthias E Liechti, Yasmin Schmid, Thomas Kraemer, Andrea E Steuer. First Time View on Human Metabolome Changes after a Single Intake of 3,4-Methylenedioxymethamphetamine in Healthy Placebo-Controlled Subjects. Journal of proteome research. 2017 09; 16(9):3310-3320. doi: 10.1021/acs.jproteome.7b00294. [PMID: 28722422]
  • Rupesh Bommana, Olivier Mozziconacci, Y John Wang, Christian Schöneich. An Efficient and Rapid Method to Monitor the Oxidative Degradation of Protein Pharmaceuticals: Probing Tyrosine Oxidation with Fluorogenic Derivatization. Pharmaceutical research. 2017 Jul; 34(7):1428-1443. doi: 10.1007/s11095-017-2159-6. [PMID: 28421307]
  • Audrey S Vanhove, Saiyu Hang, Vidhya Vijayakumar, Adam Cn Wong, John M Asara, Paula I Watnick. Vibrio cholerae ensures function of host proteins required for virulence through consumption of luminal methionine sulfoxide. PLoS pathogens. 2017 Jun; 13(6):e1006428. doi: 10.1371/journal.ppat.1006428. [PMID: 28586382]
  • Guoxiang Jiang, Lu Xiao, Huiling Yan, Dandan Zhang, Fuwang Wu, Xuncheng Liu, Xinguo Su, Xinhong Dong, Jiasheng Wang, Xuewu Duan, Yueming Jiang. Redox regulation of methionine in calmodulin affects the activity levels of senescence-related transcription factors in litchi. Biochimica et biophysica acta. General subjects. 2017 May; 1861(5 Pt A):1140-1151. doi: 10.1016/j.bbagen.2017.02.004. [PMID: 28188859]
  • Lien M Dos Santos, Tatiane M da Silva, Juliana H Azambuja, Priscila T Ramos, Pathise S Oliveira, Elita F da Silveira, Nathalia S Pedra, Kennia Galdino, Carlus A T do Couto, Mayara S P Soares, Rejane G Tavares, Roselia M Spanevello, Francieli M Stefanello, Elizandra Braganhol. Methionine and methionine sulfoxide treatment induces M1/classical macrophage polarization and modulates oxidative stress and purinergic signaling parameters. Molecular and cellular biochemistry. 2017 Jan; 424(1-2):69-78. doi: 10.1007/s11010-016-2843-6. [PMID: 27752805]
  • Mayara Sandrielly Pereira Soares, Pathise Souto Oliveira, Gabriela Nogueira Debom, Bruna da Silveira Mattos, Carla Roberta Polachini, Jucimara Baldissarelli, Vera Maria Morsch, Maria Rosa Chitolina Schetinger, Rejane Giacomelli Tavares, Francieli Moro Stefanello, Roselia Maria Spanevello. Chronic administration of methionine and/or methionine sulfoxide alters oxidative stress parameters and ALA-D activity in liver and kidney of young rats. Amino acids. 2017 01; 49(1):129-138. doi: 10.1007/s00726-016-2340-y. [PMID: 27718024]
  • Satoko Suzuki, Yoshio Kodera, Tatsuya Saito, Kazumi Fujimoto, Akari Momozono, Akinori Hayashi, Yuji Kamata, Masayoshi Shichiri. Methionine sulfoxides in serum proteins as potential clinical biomarkers of oxidative stress. Scientific reports. 2016 12; 6(?):38299. doi: 10.1038/srep38299. [PMID: 27929071]
  • Nathan J White, Yi Wang, Xiaoyun Fu, Jessica C Cardenas, Erika J Martin, Donald F Brophy, Charles E Wade, Xu Wang, Alexander E St John, Esther B Lim, Susan A Stern, Kevin R Ward, José A López, Dominic Chung. Post-translational oxidative modification of fibrinogen is associated with coagulopathy after traumatic injury. Free radical biology & medicine. 2016 07; 96(?):181-9. doi: 10.1016/j.freeradbiomed.2016.04.023. [PMID: 27105953]
  • Johannes Wüst, Monika Pischetsrieder. Methionine sulfoxide profiling of milk proteins to assess the influence of lipids on protein oxidation in milk. Food & function. 2016 Jun; 7(6):2526-36. doi: 10.1039/c5fo01550b. [PMID: 26927981]
  • Sara Samino, Maria Vinaixa, Marta Díaz, Antoni Beltran, Miguel A Rodríguez, Roger Mallol, Mercedes Heras, Anna Cabre, Lorena Garcia, Nuria Canela, Francis de Zegher, Xavier Correig, Lourdes Ibáñez, Oscar Yanes. Metabolomics reveals impaired maturation of HDL particles in adolescents with hyperinsulinaemic androgen excess. Scientific reports. 2015 Jun; 5(?):11496. doi: 10.1038/srep11496. [PMID: 26099471]
  • Silke Jacques, Bart Ghesquière, Pieter-Jan De Bock, Hans Demol, Khadija Wahni, Patrick Willems, Joris Messens, Frank Van Breusegem, Kris Gevaert. Protein Methionine Sulfoxide Dynamics in Arabidopsis thaliana under Oxidative Stress. Molecular & cellular proteomics : MCP. 2015 May; 14(5):1217-29. doi: 10.1074/mcp.m114.043729. [PMID: 25693801]
  • G Sartore, R Seraglia, S Burlina, A Bolis, R Marin, E Manzato, E Ragazzi, P Traldi, A Lapolla. High-density lipoprotein oxidation in type 2 diabetic patients and young patients with premature myocardial infarction. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2015 Apr; 25(4):418-25. doi: 10.1016/j.numecd.2014.12.004. [PMID: 25636381]
  • Yong Li, Sridhar A Malkaram, Jie Zhou, Janos Zempleni. Lysine biotinylation and methionine oxidation in the heat shock protein HSP60 synergize in the elimination of reactive oxygen species in human cell cultures. The Journal of nutritional biochemistry. 2014 Apr; 25(4):475-82. doi: 10.1016/j.jnutbio.2013.12.008. [PMID: 24582286]
  • Paul J Beisswenger, Scott K Howell, Greg Russell, Michael E Miller, Stephen S Rich, Michael Mauer. Detection of diabetic nephropathy from advanced glycation endproducts (AGEs) differs in plasma and urine, and is dependent on the method of preparation. Amino acids. 2014 Feb; 46(2):311-9. doi: 10.1007/s00726-013-1533-x. [PMID: 24036985]
  • Jackob Moskovitz. Detection and localization of methionine sulfoxide residues of specific proteins in brain tissue. Protein and peptide letters. 2014; 21(1):52-5. doi: 10.2174/09298665113209990068. [PMID: 24354771]
  • Joung Sug Kim, Hyang-Mi Park, Songhwa Chae, Tae-Ho Lee, Duk-Ju Hwang, Sung-Dug Oh, Jong-Sug Park, Dae-Geun Song, Cheol-Ho Pan, Doil Choi, Yul-Ho Kim, Baek Hie Nahm, Yeon-Ki Kim. A pepper MSRB2 gene confers drought tolerance in rice through the protection of chloroplast-targeted genes. PloS one. 2014; 9(3):e90588. doi: 10.1371/journal.pone.0090588. [PMID: 24614245]
  • Marcelo Zanusso Costa, Tatiane Morgana da Silva, Natália Porto Flores, Felipe Schmitz, Emilene Barros da Silva Scherer, Cassiana Macagnan Viau, Jenifer Saffi, Alethéa Gatto Barschak, Angela Terezinha de Souza Wyse, Roselia Maria Spanevello, Francieli Moro Stefanello. Methionine and methionine sulfoxide alter parameters of oxidative stress in the liver of young rats: in vitro and in vivo studies. Molecular and cellular biochemistry. 2013 Dec; 384(1-2):21-8. doi: 10.1007/s11010-013-1777-5. [PMID: 23963990]
  • Silke Jacques, Bart Ghesquière, Frank Van Breusegem, Kris Gevaert. Plant proteins under oxidative attack. Proteomics. 2013 Mar; 13(6):932-40. doi: 10.1002/pmic.201200237. [PMID: 23172756]
  • Roberta Seraglia, Giovanni Sartore, Raffaella Marin, Silvia Burlina, Enzo Manzato, Eugenio Ragazzi, Pietro Traldi, Annunziata Lapolla. An effective and rapid determination by MALDI/TOF/TOF of methionine sulphoxide content of ApoA-I in type 2 diabetic patients. Journal of mass spectrometry : JMS. 2013 Jan; 48(1):105-10. doi: 10.1002/jms.3113. [PMID: 23303753]
  • Dung Tien Le, Lionel Tarrago, Yasuko Watanabe, Alaattin Kaya, Byung Cheon Lee, Uyen Tran, Rie Nishiyama, Dmitri E Fomenko, Vadim N Gladyshev, Lam-Son Phan Tran. Diversity of plant methionine sulfoxide reductases B and evolution of a form specific for free methionine sulfoxide. PloS one. 2013; 8(6):e65637. doi: 10.1371/journal.pone.0065637. [PMID: 23776515]
  • Surabhi Bhatia, Bianca Knoch, Jenny Wong, Woojin S Kim, Paul L Else, Aaron J Oakley, Brett Garner. Selective reduction of hydroperoxyeicosatetraenoic acids to their hydroxy derivatives by apolipoprotein D: implications for lipid antioxidant activity and Alzheimer's disease. The Biochemical journal. 2012 Mar; 442(3):713-21. doi: 10.1042/bj20111166. [PMID: 22150111]
  • John M Ringman, Andrew T Fithian, Karen Gylys, Jeffrey L Cummings, Giovanni Coppola, David Elashoff, Domenico Pratico, Jackob Moskovitz, Gal Bitan. Plasma methionine sulfoxide in persons with familial Alzheimer's disease mutations. Dementia and geriatric cognitive disorders. 2012; 33(4):219-25. doi: 10.1159/000338546. [PMID: 22584618]
  • Marina V Kasaikina, Marina A Kravtsova, Byung Cheon Lee, Javier Seravalli, Daniel A Peterson, Jens Walter, Ryan Legge, Andrew K Benson, Dolph L Hatfield, Vadim N Gladyshev. Dietary selenium affects host selenoproteome expression by influencing the gut microbiota. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2011 Jul; 25(7):2492-9. doi: 10.1096/fj.11-181990. [PMID: 21493887]
  • Andrzej Kozik, Anna Golda, Pawel Mak, Piotr Suder, Jerzy Silberring, Anna Barbasz, Maria Rapala-Kozik. Myeloperoxidase-catalyzed oxidative inactivation of human kininogens: the impairment of kinin-precursor and prekallikrein-binding functions. Biological chemistry. 2011 Mar; 392(3):263-74. doi: 10.1515/bc.2011.021. [PMID: 21194373]
  • Harriet Mörtstedt, Marina C Jeppsson, Giovanni Ferrari, Bo A G Jönsson, Monica H Kåredal, Christian H Lindh. Strategy for identification and detection of multiple oxidative modifications within proteins applied on persulfate-oxidized hemoglobin and human serum albumin. Rapid communications in mass spectrometry : RCM. 2011 Jan; 25(2):327-40. doi: 10.1002/rcm.4867. [PMID: 21192028]
  • Xinwen Liang, Dmitri E Fomenko, Deame Hua, Alaattin Kaya, Vadim N Gladyshev. Diversity of protein and mRNA forms of mammalian methionine sulfoxide reductase B1 due to intronization and protein processing. PloS one. 2010 Jul; 5(7):e11497. doi: 10.1371/journal.pone.0011497. [PMID: 20634897]
  • Wayne Chris Hawkes, Zeynep Alkan. Regulation of redox signaling by selenoproteins. Biological trace element research. 2010 Jun; 134(3):235-51. doi: 10.1007/s12011-010-8656-7. [PMID: 20306235]
  • Edith Laugier, Lionel Tarrago, Christina Vieira Dos Santos, Françoise Eymery, Michel Havaux, Pascal Rey. Arabidopsis thaliana plastidial methionine sulfoxide reductases B, MSRBs, account for most leaf peptide MSR activity and are essential for growth under environmental constraints through a role in the preservation of photosystem antennae. The Plant journal : for cell and molecular biology. 2010 Jan; 61(2):271-82. doi: 10.1111/j.1365-313x.2009.04053.x. [PMID: 19874542]
  • Derek B Oien, Tamar Canello, Ruth Gabizon, Maria Gasset, Brandi L Lundquist, Jeff M Burns, Jackob Moskovitz. Detection of oxidized methionine in selected proteins, cellular extracts and blood serums by novel anti-methionine sulfoxide antibodies. Archives of biochemistry and biophysics. 2009 May; 485(1):35-40. doi: 10.1016/j.abb.2009.01.020. [PMID: 19388147]
  • Xiao Suo Wang, Baohai Shao, Michael N Oda, Jay W Heinecke, Stephen Mahler, Roland Stocker. A sensitive and specific ELISA detects methionine sulfoxide-containing apolipoprotein A-I in HDL. Journal of lipid research. 2009 Mar; 50(3):586-594. doi: 10.1194/jlr.d800042-jlr200. [PMID: 18832772]
  • Dmitri E Fomenko, Sergey V Novoselov, Sathish Kumar Natarajan, Byung Cheon Lee, Ahmet Koc, Bradley A Carlson, Tae-Hyung Lee, Hwa-Young Kim, Dolph L Hatfield, Vadim N Gladyshev. MsrB1 (methionine-R-sulfoxide reductase 1) knock-out mice: roles of MsrB1 in redox regulation and identification of a novel selenoprotein form. The Journal of biological chemistry. 2009 Feb; 284(9):5986-93. doi: 10.1074/jbc.m805770200. [PMID: 18990697]
  • Byung Cheon Lee, Dung Tien Le, Vadim N Gladyshev. Mammals reduce methionine-S-sulfoxide with MsrA and are unable to reduce methionine-R-sulfoxide, and this function can be restored with a yeast reductase. The Journal of biological chemistry. 2008 Oct; 283(42):28361-9. doi: 10.1074/jbc.m805059200. [PMID: 18697736]
  • Jonathan W C Brock, Alicia J Jenkins, Timothy J Lyons, Richard L Klein, Eunsil Yim, Maria Lopes-Virella, Rickey E Carter, Suzanne R Thorpe, John W Baynes. Increased methionine sulfoxide content of apoA-I in type 1 diabetes. Journal of lipid research. 2008 Apr; 49(4):847-55. doi: 10.1194/jlr.m800015-jlr200. [PMID: 18202432]
  • Maurizio Bruschi, Andrea Petretto, Giovanni Candiano, Luca Musante, Ezio Movilli, Laura Santucci, Andrea Urbani, Rosanna Gusmano, Enrico Verrina, Giovanni Cancarini, Francesco Scolari, Gian Marco Ghiggeri. Determination of the oxido-redox status of plasma albumin in hemodialysis patients. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Mar; 864(1-2):29-37. doi: 10.1016/j.jchromb.2008.01.035. [PMID: 18262857]
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