MurNAc-6-P (ECMDB24235) (M2MDB006352)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)Transporters (1)XML
Proteins (4)
Record Information
Version2.0
Creation Date2015-09-08 17:50:20 -0600
Update Date2015-09-14 16:46:10 -0600
Secondary Accession Numbers
  • ECMDB24235
Identification
Name:MurNAc-6-P
DescriptionN-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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-beta-D-glucopyranoseChEBI
N-Acetyl-beta-D-muramate 6-phosphateChEBI
2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-b-D-glucopyranoseGenerator
2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-β-D-glucopyranoseGenerator
N-Acetyl-b-D-muramate 6-phosphateGenerator
N-Acetyl-b-D-muramic acid 6-phosphoric acidGenerator
N-Acetyl-beta-D-muramic acid 6-phosphoric acidGenerator
N-Acetyl-β-D-muramate 6-phosphateGenerator
N-Acetyl-β-D-muramic acid 6-phosphoric acidGenerator
N-Acetyl-b-muramate 6-phosphateGenerator
N-Acetyl-b-muramic acid 6-phosphoric acidGenerator
N-Acetyl-beta-muramic acid 6-phosphoric acidGenerator
N-Acetyl-β-muramate 6-phosphateGenerator
N-Acetyl-β-muramic acid 6-phosphoric acidGenerator
Chemical Formula:C11H17NO11P
Weight:Average: 370.228
Monoisotopic: 370.055568109
InChI Key:NMEMTQKUEVNSPV-YVNCZSHWSA-K
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
CAS number:Not Available
IUPAC Name:(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate
Traditional IUPAC Name:(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate
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
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility42.8 g/LALOGPS
logP-1.4ALOGPS
logP-2.7ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area200.57 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity81.82 m³·mol⁻¹ChemAxon
Polarizability31.51 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
MurNAc-6-P + Water > D-Lactic acid + N-Acetylglucosamine 6-phosphate
HPr - phosphorylated + MurNAc + MurNAc > HPr + MurNAc-6-P
Adenosine triphosphate + Water + 1,6-Anhydro-N-acetylmuramate <> Adenosine diphosphate + MurNAc-6-P + ADP
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIPW000887 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-26840ebd21fec14e617eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1019000000-b294b39df58c9a255db0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9350000000-56946c4648b358d38b01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1309000000-bc198272687956621edbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ldi-9706000000-569d6ad0644babab8157View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a1479163c82b87678df2View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID58721
HMDB IDNot Available
Pubchem Compound ID45266739
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Glucose-specific phosphotransferase enzyme IIA component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
Gene Name:
crr
Uniprot ID:
P69783
Molecular weight:
18251
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
2. N-acetylmuramic acid 6-phosphate etherase
General function:
Involved in carbon-oxygen lyase activity
Specific function:
Specifically catalyzes the cleavage of the D-lactyl ether substituent of MurNAc 6-phosphate, producing GlcNAc 6- phosphate and D-lactate. Is required for growth on MurNAc as the sole source of carbon and energy. Together with AnmK, is also required for the utilization of anhydro-N-acetylmuramic acid (anhMurNAc) either imported from the medium or derived from its own cell wall murein, and thus plays a role in cell wall recycling
Gene Name:
murQ
Uniprot ID:
P76535
Molecular weight:
31220
Reactions
N-acetylmuramate 6-phosphate + H(2)O = N-acetyl-D-glucosamine 6-phosphate + D-lactate.
Protein Details
3. PTS system N-acetylmuramic acid-specific EIIBC component
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylmuramic acid (MurNAc) transport, yielding cytoplasmic MurNAc-6-P. Is responsible for growth on MurNAc as the sole source of carbon and energy. Is also able to take up anhydro-N-acetylmuramic acid (anhMurNAc), but cannot phosphorylate the carbon 6, probably because of the 1,6- anhydro ring
Gene Name:
murP
Uniprot ID:
P77272
Molecular weight:
49801
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
4. Anhydro-N-acetylmuramic acid kinase
General function:
Involved in ATP binding
Specific function:
Catalyzes the specific phosphorylation of 1,6-anhydro-N- acetylmuramic acid (anhMurNAc) with the simultaneous cleavage of the 1,6-anhydro ring, generating MurNAc-6-P. Is required for the utilization of anhMurNAc either imported from the medium or derived from its own cell wall murein, and thus plays a role in cell wall recycling
Gene Name:
anmK
Uniprot ID:
P77570
Molecular weight:
39496
Reactions
ATP + 1,6-anhydro-N-acetyl-beta-muramate + H(2)O = ADP + N-acetylmuramate 6-phosphate.

Transporters

Protein Details
1. PTS system N-acetylmuramic acid-specific EIIBC component
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylmuramic acid (MurNAc) transport, yielding cytoplasmic MurNAc-6-P. Is responsible for growth on MurNAc as the sole source of carbon and energy. Is also able to take up anhydro-N-acetylmuramic acid (anhMurNAc), but cannot phosphorylate the carbon 6, probably because of the 1,6- anhydro ring
Gene Name:
murP
Uniprot ID:
P77272
Molecular weight:
49801
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.