Record Information |
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Version | 2.0 |
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Creation Date | 2015-09-08 17:50:20 -0600 |
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Update Date | 2015-09-14 16:46:10 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | MurNAc-6-P |
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Description | N-Acetylmuramic acid 6-phosphate (MurNAc-6-P) 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: | Value | Source |
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2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-beta-D-glucopyranose | ChEBI | N-Acetyl-beta-D-muramate 6-phosphate | ChEBI | 2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-b-D-glucopyranose | Generator | 2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-β-D-glucopyranose | Generator | N-Acetyl-b-D-muramate 6-phosphate | Generator | N-Acetyl-b-D-muramic acid 6-phosphoric acid | Generator | N-Acetyl-beta-D-muramic acid 6-phosphoric acid | Generator | N-Acetyl-β-D-muramate 6-phosphate | Generator | N-Acetyl-β-D-muramic acid 6-phosphoric acid | Generator | N-Acetyl-b-muramate 6-phosphate | Generator | N-Acetyl-b-muramic acid 6-phosphoric acid | Generator | N-Acetyl-beta-muramic acid 6-phosphoric acid | Generator | N-Acetyl-β-muramate 6-phosphate | Generator | N-Acetyl-β-muramic acid 6-phosphoric acid | Generator |
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Chemical Formula: | C11H17NO11P |
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Weight: | Average: 370.228 Monoisotopic: 370.055568109 |
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InChI Key: | NMEMTQKUEVNSPV-YVNCZSHWSA-K |
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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)/p-3/t4-,6-,7-,8-,9-,11-/m1/s1 |
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CAS number: | Not Available |
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IUPAC Name: | (2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate |
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Traditional IUPAC Name: | (2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate |
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SMILES: | C[C@@H](O[C@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@@H](O)[C@@H]1NC(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
- Monosaccharide
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Alkyl phosphate
- Acetamide
- Secondary alcohol
- Carboxamide group
- Secondary carboxylic acid amide
- Hemiacetal
- Organoheterocyclic compound
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Ether
- Monocarboxylic acid or derivatives
- Oxacycle
- Organonitrogen compound
- Alcohol
- Organopnictogen compound
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Organic nitrogen compound
- Organic anion
- 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: | Amino sugar and nucleotide sugar metabolism I | PW000886 | | Amino sugar and nucleotide sugar metabolism II | PW000887 | | Amino sugar and nucleotide sugar metabolism III | PW000895 | |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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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: | Not Available |
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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: | Resource | Link |
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CHEBI ID | 58721 | HMDB ID | Not Available | Pubchem Compound ID | 45266739 | Kegg ID | Not Available | ChemSpider ID | Not Available | Wikipedia ID | Not Available | BioCyc ID | Not Available |
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