MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol (PAMDB001020)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001020
Identification
Name: MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol
Description:Murac(oyl-L-ala-D-gamma-glu-L-lys-D-ala-D-ala)-diphospho-undecaprenol is a polyprenol compound involved in the synthesis of peptidoglycan. It is a substrate for the enzyme UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase (murG). This enzyme catalyzes the transfer of a GlcNAc subunit on undecaprenyl-pyrophosphoryl-MurNAc-pentapeptide (lipid intermediate I) to form undecaprenyl-pyrophosphoryl-MurNAc-(pentapeptide)GlcNAc (lipid intermediate II). Peptidoglycan is best described as a fisherman net. The mesh of the net is made of two segments of parallel, rather inextensible glycan threads, held together by two small elastic peptide crosslinks allowing the net to expand or shrink. The glycan moiety of the peptidoglycan is remarkably uniform among all bacteria, and is made up of alternating β-1,4-linked N-acetylglucosamine and N-acetyl muramate residues, with an average chain length (in different organisms) of 10 to 65 disaccharide units. 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-α-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred by an as yet unknown mechanism 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. Peptide crosslinks form between different parts of the peptides depending on the organism. For example, in Mycobacteria and in Pseudomonas aeruginosa most links form between the carboxyl group of the penultimate D-alanine (residue 4) of one peptide to the amino group at the D-center of meso-diaminopimelate (residue 3) of an adjacent peptide of a second glycan chain (as in Pseudomonas aeruginosa). The crosslinking reaction is catalyzed by transpeptidases and involves the cleavage of the D-alanyl-D-alanine bond of the donor peptide, providing the energy to drive the reaction. As a result, the peptides in the peptidoglycan polymers are one or two amino acids shorter than the peptides in the monomers.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • MurAc(oyl-L-ala-D-g-glu-L-lys-D-ala-D-ala)-diphospho-undecaprenol
  • MurAc(oyl-L-ala-D-γ-glu-L-lys-D-ala-D-ala)-diphospho-undecaprenol
Chemical Formula: C86H143N7O21P2
Average Molecular Weight: 1673.0374
Monoisotopic Molecular Weight: 1671.981227697
InChI Key: SULOOAFLXMQJSF-SZSYZMFDSA-N
InChI:InChI=1S/C86H143N7O21P2/c1-57(2)30-20-31-58(3)32-21-33-59(4)34-22-35-60(5)36-23-37-61(6)38-24-39-62(7)40-25-41-63(8)42-26-43-64(9)44-27-45-65(10)46-28-47-66(11)48-29-49-67(12)53-55-110-115(106,107)114-116(108,109)113-86-77(91-72(17)95)79(78(97)75(56-94)112-86)111-71(16)82(100)88-69(14)81(99)93-74(85(104)105)51-52-76(96)92-73(50-18-19-54-87)83(101)89-68(13)80(98)90-70(15)84(102)103/h30,32,34,36,38,40,42,44,46,48,53,68-71,73-75,77-79,86,94,97H,18-29,31,33,35,37,39,41,43,45,47,49-52,54-56,87H2,1-17H3,(H,88,100)(H,89,101)(H,90,98)(H,91,95)(H,92,96)(H,93,99)(H,102,103)(H,104,105)(H,106,107)(H,108,109)/b58-32+,59-34+,60-36+,61-38+,62-40+,63-42+,64-44+,65-46+,66-48+,67-53+/t68-,69+,70-,71?,73+,74-,75-,77-,78-,79-,86-/m1/s1
CAS number: Not Available
IUPAC Name:(2R)-4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-1-hydroxy-2-[(1-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-6-{[hydroxy({[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene)amino]propylidene]amino}butanoic acid
Traditional IUPAC Name: (2R)-4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-1-hydroxy-2-[(1-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-6-{[hydroxy({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphoryl}oxy)phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene)amino]propylidene]amino}butanoic acid
SMILES:NCCCC[C@]([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@@](C)([H])N=C(O)C(C)([H])O[C@@]1([H])[C@@](O)([H])[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@]1([H])N=C(C)O)C(=O)O)C(O)=N[C@@](C)([H])C(O)=N[C@@](C)([H])C(=O)O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassPolyprenols
Direct Parent Polyprenyl phospho carbohydrates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl phospho carbohydrate
  • Alpha peptide
  • N-acyl-alpha-hexosamine
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Glucosamine
  • Amino sugar
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Isoprenoid phosphate
  • Alpha-amino acid or derivatives
  • Monoalkyl phosphate
  • Amino saccharide
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0013 mg/mLALOGPS
logP4.06ALOGPS
logP15.76ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area457.37 Å2ChemAxon
Rotatable Bond Count59ChemAxon
Refractivity463.45 m3·mol-1ChemAxon
Polarizability188.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate + UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) <> Uridine 5'-monophosphate + MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Uridine 5'-diphosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kbs-2130519400-23d16e0be6a43d0976d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4130123911-ed647140e3178bd7c3bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-9461301500-cdf7f4a5e117ea6dbc43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fb9-4100146209-6114570e6abc33e022b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbc-4401217219-ac639646e60225cbf4c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-6910011002-e9b9ff37048042813134View in MoNA
References
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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID23724480
Kegg IDC04851
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available