Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:31:35 -0600 |
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Update Date | 2015-06-03 17:19:28 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | N-Acetylmuramic acid 6-phosphate |
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Description | N-acetylmuramic acid 6-phosphate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. The enzyme MurQ is an N-acetylmuramic acid 6-phosphate (MurNAc 6-phosphate) hydrolase (or etherase) that hydrolyzes the lactyl side chain from MurNAc 6-phosphate and generates GlcNAc 6-phosphate. (PMID 18837509). It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. |
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Structure | |
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Synonyms: | - MurNAc 6-phosphate
- MurNAc 6-phosphoric acid
- MurNAc-6-P
- N-Acetylmuramate 6-phosphate
- N-Acetylmuramic acid 6-phosphoric acid
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Chemical Formula: | C11H20NO11P |
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Weight: | Average: 373.2504 Monoisotopic: 373.077396999 |
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InChI Key: | NMEMTQKUEVNSPV-MKFCKLDKSA-N |
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InChI: | InChI=1S/C11H20NO11P/c1-4(10(15)16)22-9-7(12-5(2)13)11(17)23-6(8(9)14)3-21-24(18,19)20/h4,6-9,11,14,17H,3H2,1-2H3,(H,12,13)(H,15,16)(H2,18,19,20)/t4-,6-,7-,8-,9-,11?/m1/s1 |
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CAS number: | Not Available |
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IUPAC Name: | (2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-4-yl]oxy}propanoic acid |
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Traditional IUPAC Name: | MurNAc 6-phosphate |
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SMILES: | [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(COP(O)(O)=O)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Acylaminosugars |
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Alternative Parents | |
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Substituents | - Acylaminosugar
- Muramic_acid
- Hexose phosphate
- N-acyl-alpha-hexosamine
- Hexose monosaccharide
- Monosaccharide phosphate
- Sugar acid
- Monoalkyl phosphate
- Monosaccharide
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Alkyl phosphate
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Hemiacetal
- Organoheterocyclic compound
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Ether
- Oxacycle
- Monocarboxylic acid or derivatives
- Organonitrogen compound
- Alcohol
- Carbonyl group
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Not Available |
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Charge: | -3 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - Amino sugar and nucleotide sugar metabolism ec00520
- Phosphotransferase system (PTS) ec02060
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EcoCyc Pathways: | - 1,6-anhydro-N-acetylmuramic acid recycling PWY0-1261
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | |
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References |
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References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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