Keto-3-deoxy-D-manno-octulosonic acid (BioDeep_00000172544)

Main id: BioDeep_00000004607

 

human metabolite blood metabolite Volatile Flavor Compounds


代谢物信息卡片


Ion(1-),(D)-isomer OF 2-keto-3-deoxyoctonate

化学式: C8H14O8 (238.0688644)
中文名称: 2-酮基-3-脱氧辛酮酸铵盐
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C(C(C(C(CO)O)O)O)O)C(=O)C(=O)O
InChI: InChI=1S/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)

描述信息

同义名列表

22 个代谢物同义名

Ion(1-),(D)-isomer OF 2-keto-3-deoxyoctonate; (D-Manno)-isomer OF 2-keto-3-deoxyoctonate; 4,5,6,7,8-pentahydroxy-2-oxooctanoic acid; 3-Deoxy-alpha-D-manno-2-octulosonic acid; Keto-3-deoxy-D-manno-octulosonic acid; 4,5,6,7,8-Pentahydroxy-2-oxooctanoate; 3-Deoxy-8-manno-oct-2-ulosonic acid; 3-Deoxy-D-manno-oct-2-ulosonic acid; 2-Keto-3-deoxy-D-manno-octonic acid; Keto-3-deoxy-D-manno-octulosonate; 3-Deoxy-D-manno-octulosonic acid; 2-Keto-3-deoxyoctulosonic acid; 3-deoxy-D-manno-octulosonate; 3-Deoxy-D-mannooctulosonate; 3-Deoxy-2-octulosonic acid; 3-Deoxy-D-mannoctulosonate; 2-Keto-3-deoxyoctonate; 3-Deoxyoctulosonate; KDO CPD; 3-KDO; 3-Deoxy-D-manno-octulosonate; 2-Keto-3-deoxyoctonic acid



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

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。



文献列表

  • Addison G DeBoer, Lei Lei, Chunfu Yang, Craig A Martens, Sarah L Anzick, Sophia Antonioli-Schmit, Robert J Suchland, Grant McClarty, Harlan D Caldwell, Daniel D Rockey. TargeTron Inactivation of Chlamydia trachomatis gseA Results in a Lipopolysaccharide 3-Deoxy-d-Manno-Oct-2-Ulosonic Acid-Deficient Strain That Is Cytotoxic for Cells. Infection and immunity. 2023 May; ?(?):e0009623. doi: 10.1128/iai.00096-23. [PMID: 37255490]
  • Gianluigi De Benedetto, Francesca Micoli, Silvia Londero, Laura Salvini, Luisa Sturiale, Domenico Garozzo, Neil Ravenscroft, Carlo Giannelli, Paola Cescutti. Characterization of the Salmonella Typhimurium core oligosaccharide and its reducing end 3-deoxy-d-manno-oct-2-ulosonic acid used for conjugate vaccine production. Carbohydrate research. 2019 Jul; 481(?):43-51. doi: 10.1016/j.carres.2019.05.014. [PMID: 31228656]
  • Wei Huang, Ying-Yu Zhou, Xing-Ling Pan, Xian-Yang Zhou, Jin-Cai Lei, Dong-Mei Liu, Yue Chu, Jin-Song Yang. Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d- manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides. Journal of the American Chemical Society. 2018 03; 140(10):3574-3582. doi: 10.1021/jacs.7b09461. [PMID: 29481074]
  • Marina Harper, Amy Wright, Frank St Michael, Jianjun Li, Deanna Deveson Lucas, Mark Ford, Ben Adler, Andrew D Cox, John D Boyce. Characterization of Two Novel Lipopolysaccharide Phosphoethanolamine Transferases in Pasteurella multocida and Their Role in Resistance to Cathelicidin-2. Infection and immunity. 2017 11; 85(11):. doi: 10.1128/iai.00557-17. [PMID: 28874446]
  • Liuqing Wen, Yuan Zheng, Tiehai Li, Peng George Wang. Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly. Bioorganic & medicinal chemistry letters. 2016 Jun; 26(12):2825-2828. doi: 10.1016/j.bmcl.2016.04.061. [PMID: 27173798]
  • Olga G Ovchinnikova, Evan Mallette, Akihiko Koizumi, Todd L Lowary, Matthew S Kimber, Chris Whitfield. Bacterial β-Kdo glycosyltransferases represent a new glycosyltransferase family (GT99). Proceedings of the National Academy of Sciences of the United States of America. 2016 May; 113(22):E3120-9. doi: 10.1073/pnas.1603146113. [PMID: 27199480]
  • Akintunde Emiola, Steven S Andrews, Carolin Heller, John George. Crosstalk between the lipopolysaccharide and phospholipid pathways during outer membrane biogenesis in Escherichia coli. Proceedings of the National Academy of Sciences of the United States of America. 2016 Mar; 113(11):3108-13. doi: 10.1073/pnas.1521168113. [PMID: 26929331]
  • Marie Dumont, Arnaud Lehner, Boris Vauzeilles, Julien Malassis, Alan Marchant, Kevin Smyth, Bruno Linclau, Aurélie Baron, Jordi Mas Pons, Charles T Anderson, Damien Schapman, Ludovic Galas, Jean-Claude Mollet, Patrice Lerouge. Plant cell wall imaging by metabolic click-mediated labelling of rhamnogalacturonan II using azido 3-deoxy-D-manno-oct-2-ulosonic acid. The Plant journal : for cell and molecular biology. 2016 Feb; 85(3):437-47. doi: 10.1111/tpj.13104. [PMID: 26676799]
  • Tetsuto Nakagawa, Yoshimi Shimada, Nadejda V Pavlova, Su-Chen Li, Yu-Teh Li. Cloning and expression of 3-deoxy-d-manno-oct-2-ulosonic acid α-ketoside hydrolase from oyster hepatopancreas†. Glycobiology. 2015 Dec; 25(12):1431-40. doi: 10.1093/glycob/cwv074. [PMID: 26362869]
  • Uwe Mamat, Kathleen Wilke, David Bramhill, Andra Beate Schromm, Buko Lindner, Thomas Andreas Kohl, José Luis Corchero, Antonio Villaverde, Lana Schaffer, Steven Robert Head, Chad Souvignier, Timothy Charles Meredith, Ronald Wesley Woodard. Detoxifying Escherichia coli for endotoxin-free production of recombinant proteins. Microbial cell factories. 2015 Apr; 14(?):57. doi: 10.1186/s12934-015-0241-5. [PMID: 25890161]
  • Marie Dumont, Arnaud Lehner, Sophie Bouton, Marie Christine Kiefer-Meyer, Aline Voxeur, Jérôme Pelloux, Patrice Lerouge, Jean-Claude Mollet. The cell wall pectic polymer rhamnogalacturonan-II is required for proper pollen tube elongation: implications of a putative sialyltransferase-like protein. Annals of botany. 2014 Oct; 114(6):1177-88. doi: 10.1093/aob/mcu093. [PMID: 24825296]
  • Erica J Rubin, John P O'Brien, Petko L Ivanov, Jennifer S Brodbelt, M Stephen Trent. Identification of a broad family of lipid A late acyltransferases with non-canonical substrate specificity. Molecular microbiology. 2014 Mar; 91(5):887-99. doi: 10.1111/mmi.12501. [PMID: 24372821]
  • Lisa M Willis, Chris Whitfield. KpsC and KpsS are retaining 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) transferases involved in synthesis of bacterial capsules. Proceedings of the National Academy of Sciences of the United States of America. 2013 Dec; 110(51):20753-8. doi: 10.1073/pnas.1312637110. [PMID: 24302764]
  • Jolanta Lodowska, Daniel Wolny, Ludmiła Węglarz. The sugar 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) as a characteristic component of bacterial endotoxin -- a review of its biosynthesis, function, and placement in the lipopolysaccharide core. Canadian journal of microbiology. 2013 Oct; 59(10):645-55. doi: 10.1139/cjm-2013-0490. [PMID: 24102217]
  • Malin Vonkavaara, Shaikh Terkis Islam Pavel, Kathrin Hölzl, Roland Nordfelth, Anders Sjöstedt, Svenja Stöven. Francisella is sensitive to insect antimicrobial peptides. Journal of innate immunity. 2013; 5(1):50-9. doi: 10.1159/000342468. [PMID: 23037919]
  • Gulden Camci-Unal, Rahman M Mizanur, Yonghai Chai, Nicola L B Pohl. Synthesis of a 3-deoxy-D-manno-octulosonic acid (KDO) building block from D-glucose via fermentation. Organic & biomolecular chemistry. 2012 Aug; 10(30):5856-60. doi: 10.1039/c2ob25168j. [PMID: 22505005]
  • Yukari Fujimoto, Atsushi Shimoyama, Yasuo Suda, Koichi Fukase. Synthesis and immunomodulatory activities of Helicobacter pylori lipophilic terminus of lipopolysaccharide including lipid A. Carbohydrate research. 2012 Jul; 356(?):37-43. doi: 10.1016/j.carres.2012.03.013. [PMID: 22486825]
  • Ken Shiraiwa, Shen Yuan, Ayako Fujiyama, Yosuke Matsuo, Takashi Tanaka, Zhi-Hong Jiang, Isao Kouno. Benzyl benzoate glycoside and 3-deoxy-D-manno-2-octulosonic acid derivatives from Solidago decurrens. Journal of natural products. 2012 Jan; 75(1):88-92. doi: 10.1021/np2007582. [PMID: 22185651]
  • Simon Ittig, Buko Lindner, Marco Stenta, Pablo Manfredi, Evelina Zdorovenko, Yuriy A Knirel, Matteo dal Peraro, Guy R Cornelis, Ulrich Zähringer. The lipopolysaccharide from Capnocytophaga canimorsus reveals an unexpected role of the core-oligosaccharide in MD-2 binding. PLoS pathogens. 2012; 8(5):e1002667. doi: 10.1371/journal.ppat.1002667. [PMID: 22570611]
  • Maor Bar-Peled, Breeanna R Urbanowicz, Malcolm A O'Neill. The Synthesis and Origin of the Pectic Polysaccharide Rhamnogalacturonan II - Insights from Nucleotide Sugar Formation and Diversity. Frontiers in plant science. 2012; 3(?):92. doi: 10.3389/fpls.2012.00092. [PMID: 22639675]
  • Masaru Kobayashi, Nagisa Kouzu, Akina Inami, Kiminori Toyooka, Yuki Konishi, Ken Matsuoka, Toru Matoh. Characterization of Arabidopsis CTP:3-deoxy-D-manno-2-octulosonate cytidylyltransferase (CMP-KDO synthetase), the enzyme that activates KDO during rhamnogalacturonan II biosynthesis. Plant & cell physiology. 2011 Oct; 52(10):1832-43. doi: 10.1093/pcp/pcr120. [PMID: 21893514]
  • Yasunori Isshiki, Seiichi Kondo. Characterization of the carbohydrate backbone of Vibrio parahaemolyticus O6 lipopolysaccharides. Microbiology and immunology. 2011 Aug; 55(8):539-51. doi: 10.1111/j.1348-0421.2011.00355.x. [PMID: 21639862]
  • D Kocíncová, J S Lam. Structural diversity of the core oligosaccharide domain of Pseudomonas aeruginosa lipopolysaccharide. Biochemistry. Biokhimiia. 2011 Jul; 76(7):755-60. doi: 10.1134/s0006297911070054. [PMID: 21999536]
  • Hak Suk Chung, Christian R H Raetz. Dioxygenases in Burkholderia ambifaria and Yersinia pestis that hydroxylate the outer Kdo unit of lipopolysaccharide. Proceedings of the National Academy of Sciences of the United States of America. 2011 Jan; 108(2):510-5. doi: 10.1073/pnas.1016462108. [PMID: 21178073]
  • Joanna Kubler-Kielb. Conjugation of LPS-derived oligosaccharides to proteins using oxime chemistry. Methods in molecular biology (Clifton, N.J.). 2011; 751(?):317-27. doi: 10.1007/978-1-61779-151-2_20. [PMID: 21674340]
  • L Cipolla, A Polissi, C Airoldi, L Gabrielli, S Merlo, F Nicotra. New targets for antibacterial design: Kdo biosynthesis and LPS machinery transport to the cell surface. Current medicinal chemistry. 2011; 18(6):830-52. doi: 10.2174/092986711794927676. [PMID: 21182480]
  • Christopher M Stead, Jinshi Zhao, Christian R H Raetz, M Stephen Trent. Removal of the outer Kdo from Helicobacter pylori lipopolysaccharide and its impact on the bacterial surface. Molecular microbiology. 2010 Nov; 78(4):837-52. doi: 10.1111/j.1365-2958.2010.07304.x. [PMID: 20659292]
  • Flavien Dardelle, Arnaud Lehner, Yasmina Ramdani, Muriel Bardor, Patrice Lerouge, Azeddine Driouich, Jean-Claude Mollet. Biochemical and immunocytological characterizations of Arabidopsis pollen tube cell wall. Plant physiology. 2010 Aug; 153(4):1563-76. doi: 10.1104/pp.110.158881. [PMID: 20547702]
  • Martial Séveno, Emilie Séveno-Carpentier, Aline Voxeur, Laurence Menu-Bouaouiche, Christophe Rihouey, Frédéric Delmas, Christian Chevalier, Azeddine Driouich, Patrice Lerouge. Characterization of a putative 3-deoxy-D-manno-2-octulosonic acid (Kdo) transferase gene from Arabidopsis thaliana. Glycobiology. 2010 May; 20(5):617-28. doi: 10.1093/glycob/cwq011. [PMID: 20124190]
  • Gabriela Bugla-Płoskońska, Jacek Rybka, Bozena Futoma-Kołoch, Agnieszka Cisowska, Andrzej Gamian, Włodzimierz Doroszkiewicz. Sialic acid-containing lipopolysaccharides of Salmonella O48 strains--potential role in camouflage and susceptibility to the bactericidal effect of normal human serum. Microbial ecology. 2010 Apr; 59(3):601-13. doi: 10.1007/s00248-009-9600-2. [PMID: 19844648]
  • Adrienn Pálvölgyi, Veronika Deák, Véréna Poinsot, Tibor Nagy, Enik Nagy, Ildikó Kerepesi, Péter Putnoky. Genetic analysis of the rkp-3 gene region in Sinorhizobium meliloti 41: rkpY directs capsular polysaccharide synthesis to KR5 antigen production. Molecular plant-microbe interactions : MPMI. 2009 Nov; 22(11):1422-30. doi: 10.1094/mpmi-22-11-1422. [PMID: 19810811]
  • Silvia Sommaruga, Luca De Gioia, Paolo Tortora, Alessandra Polissi. Structure prediction and functional analysis of KdsD, an enzyme involved in lipopolysaccharide biosynthesis. Biochemical and biophysical research communications. 2009 Oct; 388(2):222-7. doi: 10.1016/j.bbrc.2009.07.154. [PMID: 19664604]
  • Jessica V Hankins, M Stephen Trent. Secondary acylation of Vibrio cholerae lipopolysaccharide requires phosphorylation of Kdo. The Journal of biological chemistry. 2009 Sep; 284(38):25804-12. doi: 10.1074/jbc.m109.022772. [PMID: 19617350]
  • Gracjana Klein, Buko Lindner, Werner Brabetz, Helmut Brade, Satish Raina. Escherichia coli K-12 Suppressor-free Mutants Lacking Early Glycosyltransferases and Late Acyltransferases: minimal lipopolysaccharide structure and induction of envelope stress response. The Journal of biological chemistry. 2009 Jun; 284(23):15369-89. doi: 10.1074/jbc.m900490200. [PMID: 19346244]
  • Hussein Masoud, Malcolm B Perry, Jean-Robert Brisson, Dusan Uhrin, Jianjun Li, James C Richards. Structural elucidation of the novel core oligosaccharide from LPS of Burkholderia cepacia serogroup O4. Glycobiology. 2009 May; 19(5):462-71. doi: 10.1093/glycob/cwn155. [PMID: 19141607]
  • Constance M John, Mingfeng Liu, Gary A Jarvis. Profiles of structural heterogeneity in native lipooligosaccharides of Neisseria and cytokine induction. Journal of lipid research. 2009 Mar; 50(3):424-438. doi: 10.1194/jlr.m800184-jlr200. [PMID: 18832773]
  • Mark J Karbarz, David A Six, Christian R H Raetz. Purification and characterization of the lipid A 1-phosphatase LpxE of Rhizobium leguminosarum. The Journal of biological chemistry. 2009 Jan; 284(1):414-425. doi: 10.1074/jbc.m808390200. [PMID: 18984595]
  • Jolanta Lodowska, Daniel Wolny, Marzena Jaworska-Kik, Zofia Dzierzewicz, Ludmiła Weglarz. Interstrain diversity of 2-keto-3-deoxyoctonate content in lipopolysaccharides of Desulfovibrio desulfuricans. Polish journal of microbiology. 2009; 58(1):21-7. doi: . [PMID: 19469282]
  • Chen Katz, Eliora Z Ron. Dual role of FtsH in regulating lipopolysaccharide biosynthesis in Escherichia coli. Journal of bacteriology. 2008 Nov; 190(21):7117-22. doi: 10.1128/jb.00871-08. [PMID: 18776015]
  • Johanna M Schwingel, Frank St Michael, Andrew D Cox, Hussein Masoud, James C Richards, Anthony A Campagnari. A unique glycosyltransferase involved in the initial assembly of Moraxella catarrhalis lipooligosaccharides. Glycobiology. 2008 Jun; 18(6):447-55. doi: 10.1093/glycob/cwn021. [PMID: 18337458]
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  • Sanaa Fadel, Adrian Eley. Is lipopolysaccharide a factor in infectivity of Chlamydia trachomatis?. Journal of medical microbiology. 2008 Mar; 57(Pt 3):261-266. doi: 10.1099/jmm.0.47237-0. [PMID: 18287286]
  • Uwe Mamat, Timothy C Meredith, Parag Aggarwal, Annika Kühl, Paul Kirchhoff, Buko Lindner, Anna Hanuszkiewicz, Jennifer Sun, Otto Holst, Ronald W Woodard. Single amino acid substitutions in either YhjD or MsbA confer viability to 3-deoxy-d-manno-oct-2-ulosonic acid-depleted Escherichia coli. Molecular microbiology. 2008 Feb; 67(3):633-48. doi: 10.1111/j.1365-2958.2007.06074.x. [PMID: 18093093]
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  • Frédéric Delmas, Martial Séveno, Julian G B Northey, Michel Hernould, Patrice Lerouge, Peter McCourt, Christian Chevalier. The synthesis of the rhamnogalacturonan II component 3-deoxy-D-manno-2-octulosonic acid (Kdo) is required for pollen tube growth and elongation. Journal of experimental botany. 2008; 59(10):2639-47. doi: 10.1093/jxb/ern118. [PMID: 18503041]
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