UDP-N-acetyl-α-D-muramic acid (BioDeep_00001870050)
Main id: BioDeep_00000004552
代谢物信息卡片
(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoic acid
化学式: C20H31N3O19P2 (679.1027)
中文名称: UDP-N-乙酰胞壁酸
谱图信息:
最多检出来源 () 0%
Reviewed
Last reviewed on 2024-12-16.
Cite this Page
UDP-N-acetyl-α-D-muramic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/udp-n-acetyl-α-d-muramic_acid (retrieved
2024-12-22) (BioDeep RN: BioDeep_00001870050). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CC(C(=O)O)OC1C(C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)NC(=O)C
InChI: InChI=1S/C20H31N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/t7-,9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1
描述信息
UDP-N-acetyl-alpha-D-muramic acid is a UDP-N-acetyl-D-muramate in which the anomeric centre of the pyranose fragment has alpha-configuration. It is a conjugate acid of an UDP-N-acetyl-alpha-D-muramate(3-).
A nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It serves as the building block upon which peptidoglycan is formed.
同义名列表
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:70765
- KEGG: C01050
- PubChem: 11006912
- CAS: 18867-75-9
- PubChem: 4292
- PDB-CCD: EPZ
- 3DMET: B04759
- NIKKAJI: J710.466I
分类词条
相关代谢途径
Reactome(0)
BioCyc(2)
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
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10.1002/anie.201603441. [PMID: 27225706] - Sarah Witzke, Michael Petersen, Timothy S Carpenter, Syma Khalid. Molecular Dynamics Simulations Reveal the Conformational Flexibility of Lipid II and Its Loose Association with the Defensin Plectasin in the Staphylococcus aureus Membrane.
Biochemistry.
2016 06; 55(23):3303-14. doi:
10.1021/acs.biochem.5b01315. [PMID: 27158738] - Ben C Chung, Ellene H Mashalidis, Tetsuya Tanino, Mijung Kim, Akira Matsuda, Jiyong Hong, Satoshi Ichikawa, Seok-Yong Lee. Structural insights into inhibition of lipid I production in bacterial cell wall synthesis.
Nature.
2016 05; 533(7604):557-560. doi:
10.1038/nature17636. [PMID: 27088606] - Paulina Schmitt, Rafael D Rosa, Delphine Destoumieux-Garzón. An intimate link between antimicrobial peptide sequence diversity and binding to essential components of bacterial membranes.
Biochimica et biophysica acta.
2016 May; 1858(5):958-70. doi:
10.1016/j.bbamem.2015.10.011. [PMID: 26498397] - Sabine F Oppedijk, Nathaniel I Martin, Eefjan Breukink. Hit 'em where it hurts: The growing and structurally diverse family of peptides that target lipid-II.
Biochimica et biophysica acta.
2016 May; 1858(5):947-57. doi:
10.1016/j.bbamem.2015.10.024. [PMID: 26523408] - Laurens H J Kleijn, Sabine F Oppedijk, Peter 't Hart, Roel M van Harten, Leah A Martin-Visscher, Johan Kemmink, Eefjan Breukink, Nathaniel I Martin. Total Synthesis of Laspartomycin C and Characterization of Its Antibacterial Mechanism of Action.
Journal of medicinal chemistry.
2016 Apr; 59(7):3569-74. doi:
10.1021/acs.jmedchem.6b00219. [PMID: 26967152] - Matthew A Jorgenson, Suresh Kannan, Mary E Laubacher, Kevin D Young. Dead-end intermediates in the enterobacterial common antigen pathway induce morphological defects in Escherichia coli by competing for undecaprenyl phosphate.
Molecular microbiology.
2016 Apr; 100(1):1-14. doi:
10.1111/mmi.13284. [PMID: 26593043] - Sonia I Maffioli, João C S Cruz, Paolo Monciardini, Margherita Sosio, Stefano Donadio. Advancing cell wall inhibitors towards clinical applications.
Journal of industrial microbiology & biotechnology.
2016 Mar; 43(2-3):177-84. doi:
10.1007/s10295-015-1703-9. [PMID: 26515981] - Sam Mulholland, Eleanor R Turpin, Boyan B Bonev, Jonathan D Hirst. Docking and molecular dynamics simulations of the ternary complex nisin2:lipid II.
Scientific reports.
2016 Feb; 6(?):21185. doi:
10.1038/srep21185. [PMID: 26888784] - Erik Henrich, Yi Ma, Ina Engels, Daniela Münch, Christian Otten, Tanja Schneider, Beate Henrichfreise, Hans-Georg Sahl, Volker Dötsch, Frank Bernhard. Lipid Requirements for the Enzymatic Activity of MraY Translocases and in Vitro Reconstitution of the Lipid II Synthesis Pathway.
The Journal of biological chemistry.
2016 Jan; 291(5):2535-46. doi:
10.1074/jbc.m115.664292. [PMID: 26620564] - Peter 't Hart, Sabine F Oppedijk, Eefjan Breukink, Nathaniel I Martin. New Insights into Nisin's Antibacterial Mechanism Revealed by Binding Studies with Synthetic Lipid II Analogues.
Biochemistry.
2016 Jan; 55(1):232-7. doi:
10.1021/acs.biochem.5b01173. [PMID: 26653142] - Izidor Sosič, Marko Anderluh, Matej Sova, Martina Gobec, Irena Mlinarič Raščan, Adeline Derouaux, Ana Amoroso, Mohammed Terrak, Eefjan Breukink, Stanislav Gobec. Structure-Activity Relationships of Novel Tryptamine-Based Inhibitors of Bacterial Transglycosylase.
Journal of medicinal chemistry.
2015 Dec; 58(24):9712-21. doi:
10.1021/acs.jmedchem.5b01482. [PMID: 26588190] - Daniela Münch, Hans-Georg Sahl. Structural variations of the cell wall precursor lipid II in Gram-positive bacteria - Impact on binding and efficacy of antimicrobial peptides.
Biochimica et biophysica acta.
2015 Nov; 1848(11 Pt B):3062-71. doi:
10.1016/j.bbamem.2015.04.014. [PMID: 25934055] - Tobias Spieß, Sophie Marianne Korn, Peter Kötter, Karl-Dieter Entian. Activation of Histidine Kinase SpaK Is Mediated by the N-Terminal Portion of Subtilin-Like Lantibiotics and Is Independent of Lipid II.
Applied and environmental microbiology.
2015 Aug; 81(16):5335-43. doi:
10.1128/aem.01368-15. [PMID: 26025904] - Timo Koopmans, Thomas M Wood, Peter 't Hart, Laurens H J Kleijn, Antoni P A Hendrickx, Rob J L Willems, Eefjan Breukink, Nathaniel I Martin. Semisynthetic Lipopeptides Derived from Nisin Display Antibacterial Activity and Lipid II Binding on Par with That of the Parent Compound.
Journal of the American Chemical Society.
2015 Jul; 137(29):9382-9. doi:
10.1021/jacs.5b04501. [PMID: 26122963] - Jack C Slootweg, Eric F van Herwerden, Mark F M van Doremalen, Eefjan Breukink, Rob M J Liskamp, Dirk T S Rijkers. Synthesis of nisin AB dicarba analogs using ring-closing metathesis: influence of sp(3) versus sp(2) hybridization of the α-carbon atom of residues dehydrobutyrine-2 and dehydroalanine-5 on the lipid II binding affinity.
Organic & biomolecular chemistry.
2015 Jun; 13(21):5997-6009. doi:
10.1039/c5ob00336a. [PMID: 25940216] - Alexander J Meeske, Lok-To Sham, Harvey Kimsey, Byoung-Mo Koo, Carol A Gross, Thomas G Bernhardt, David Z Rudner. MurJ and a novel lipid II flippase are required for cell wall biogenesis in Bacillus subtilis.
Proceedings of the National Academy of Sciences of the United States of America.
2015 May; 112(20):6437-42. doi:
10.1073/pnas.1504967112. [PMID: 25918422] - Evi Stegmann, Hans-Joerg Frasch, Regina Kilian, Roberta Pozzi. Self-resistance mechanisms of actinomycetes producing lipid II-targeting antibiotics.
International journal of medical microbiology : IJMM.
2015 Feb; 305(2):190-5. doi:
10.1016/j.ijmm.2014.12.015. [PMID: 25601631] - Menno B Tol, Danae Morales Angeles, Dirk-Jan Scheffers. In vivo cluster formation of nisin and lipid II is correlated with membrane depolarization.
Antimicrobial agents and chemotherapy.
2015; 59(6):3683-6. doi:
10.1128/aac.04781-14. [PMID: 25870072] - Steven Fletcher, Wenbo Yu, Jing Huang, Steven M Kwasny, Jay Chauhan, Timothy J Opperman, Alexander D MacKerell, Erik P H de Leeuw. Structure-activity exploration of a small-molecule Lipid II inhibitor.
Drug design, development and therapy.
2015; 9(?):2383-94. doi:
10.2147/dddt.s79504. [PMID: 25987836] - Emily K Butler, Wee Boon Tan, Hildy Joseph, Natividad Ruiz. Charge requirements of lipid II flippase activity in Escherichia coli.
Journal of bacteriology.
2014 Dec; 196(23):4111-9. doi:
10.1128/jb.02172-14. [PMID: 25225268] - Yuan Qiao, Matthew D Lebar, Kathrin Schirner, Kaitlin Schaefer, Hirokazu Tsukamoto, Daniel Kahne, Suzanne Walker. Detection of lipid-linked peptidoglycan precursors by exploiting an unexpected transpeptidase reaction.
Journal of the American Chemical Society.
2014 Oct; 136(42):14678-81. doi:
10.1021/ja508147s. [PMID: 25291014] - Matthew D Lebar, Janine M May, Alexander J Meeske, Sara A Leiman, Tania J Lupoli, Hirokazu Tsukamoto, Richard Losick, David Z Rudner, Suzanne Walker, Daniel Kahne. Reconstitution of peptidoglycan cross-linking leads to improved fluorescent probes of cell wall synthesis.
Journal of the American Chemical Society.
2014 Aug; 136(31):10874-7. doi:
10.1021/ja505668f. [PMID: 25036369] - Darren Braddick, Sandeep Sandhu, David I Roper, Michael J Chappell, Timothy D H Bugg. Observation of the time-course for peptidoglycan lipid intermediate II polymerization by Staphylococcus aureus monofunctional transglycosylase.
Microbiology (Reading, England).
2014 Aug; 160(Pt 8):1628-1636. doi:
10.1099/mic.0.079442-0. [PMID: 24858082] - Lin-Ya Huang, Shih-Hsien Huang, Ya-Chih Chang, Wei-Chieh Cheng, Ting-Jen R Cheng, Chi-Huey Wong. Enzymatic synthesis of lipid II and analogues.
Angewandte Chemie (International ed. in English).
2014 Jul; 53(31):8060-5. doi:
10.1002/anie.201402313. [PMID: 24990652] - Lok-To Sham, Emily K Butler, Matthew D Lebar, Daniel Kahne, Thomas G Bernhardt, Natividad Ruiz. Bacterial cell wall. MurJ is the flippase of lipid-linked precursors for peptidoglycan biogenesis.
Science (New York, N.Y.).
2014 Jul; 345(6193):220-2. doi:
10.1126/science.1254522. [PMID: 25013077] - Yasmine Fathy Mohamed, Miguel A Valvano. A Burkholderia cenocepacia MurJ (MviN) homolog is essential for cell wall peptidoglycan synthesis and bacterial viability.
Glycobiology.
2014 Jun; 24(6):564-76. doi:
10.1093/glycob/cwu025. [PMID: 24688094] - Tamimount Mohammadi, Robert Sijbrandi, Mandy Lutters, Jolanda Verheul, Nathaniel I Martin, Tanneke den Blaauwen, Ben de Kruijff, Eefjan Breukink. Specificity of the transport of lipid II by FtsW in Escherichia coli.
The Journal of biological chemistry.
2014 May; 289(21):14707-18. doi:
10.1074/jbc.m114.557371. [PMID: 24711460] - Hiroki Kinouchi, Hirokazu Arimoto, Kenzo Nishiguchi, Masako Oka, Hideki Maki, Hiroshi Kitagawa, Hiroshi Kamimori. Binding properties of antimicrobial agents to dipeptide terminal of lipid II using surface plasmon resonance.
Analytical biochemistry.
2014 May; 452(?):67-75. doi:
10.1016/j.ab.2014.02.012. [PMID: 24556247] - Katsuhiko Mitachi, Priya Mohan, Shajila Siricilla, Michio Kurosu. One-pot protection-glycosylation reactions for synthesis of lipid II analogues.
Chemistry (Weinheim an der Bergstrasse, Germany).
2014 Apr; 20(16):4554-8. doi:
10.1002/chem.201400307. [PMID: 24623584] - Nicolas Jacquier, Antonio Frandi, Trestan Pillonel, Patrick H Viollier, Patrick Viollier, Gilbert Greub. Cell wall precursors are required to organize the chlamydial division septum.
Nature communications.
2014 Apr; 5(?):3578. doi:
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Protein and peptide letters.
2014 Apr; 21(4):336-40. doi:
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PloS one.
2014; 9(7):e102246. doi:
10.1371/journal.pone.0102246. [PMID: 25014359] - Erik P H de Leeuw. Efficacy of the small molecule inhibitor of Lipid II BAS00127538 against Acinetobacter baumannii.
Drug design, development and therapy.
2014; 8(?):1061-4. doi:
10.2147/dddt.s68020. [PMID: 25143710] - André Zapun, Jules Philippe, Katherine A Abrahams, Luca Signor, David I Roper, Eefjan Breukink, Thierry Vernet. In vitro reconstitution of peptidoglycan assembly from the Gram-positive pathogen Streptococcus pneumoniae.
ACS chemical biology.
2013 Dec; 8(12):2688-96. doi:
10.1021/cb400575t. [PMID: 24044435] - Boris Sieger, Karin Schubert, Catriona Donovan, Marc Bramkamp. The lipid II flippase RodA determines morphology and growth in Corynebacterium glutamicum.
Molecular microbiology.
2013 Dec; 90(5):966-82. doi:
10.1111/mmi.12411. [PMID: 24118443] - Shih-Hsien Huang, Wei-Shen Wu, Lin-Ya Huang, Wen-Feng Huang, Wei-Chen Fu, Po-Ting Chen, Jim-Min Fang, Wei-Chieh Cheng, Ting-Jen R Cheng, Chi-Huey Wong. New continuous fluorometric assay for bacterial transglycosylase using Förster resonance energy transfer.
Journal of the American Chemical Society.
2013 Nov; 135(45):17078-89. doi:
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Molecular microbiology.
2013 Nov; 90(3):502-18. doi:
10.1111/mmi.12380. [PMID: 23980836] - Jennifer Shepherd, Michael Ibba. Lipid II-independent trans editing of mischarged tRNAs by the penicillin resistance factor MurM.
The Journal of biological chemistry.
2013 Sep; 288(36):25915-25923. doi:
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