MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol (ECMDB20173) (M2MDB001020)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (843)
Record Information
Version2.0
Creation Date2012-05-31 14:31:23 -0600
Update Date2015-06-03 17:19:27 -0600
Secondary Accession Numbers
  • ECMDB20173
Identification
Name:MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol
DescriptionMurac(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 E. coli 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 E. coli). 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
MOLSDFPDBSMILESInChI
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
Weight:Average: 1673.0374
Monoisotopic: 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
Description belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenyl phospho carbohydrates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl phospho carbohydrate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • Alpha peptide
  • N-acyl-alpha-hexosamine
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hexose monosaccharide
  • Alanine or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Isoprenoid phosphate
  • Alpha-amino acid or derivatives
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Amino acid or derivatives
  • 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
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count59ChemAxon
Refractivity463.45 m³·mol⁻¹ChemAxon
Polarizability188.57 ųChemAxon
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
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
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

Enzymes

Protein Details
1. Phospho-N-acetylmuramoyl-pentapeptide-transferase
General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
First step of the lipid cycle reactions in the biosynthesis of the cell wall peptidoglycan
Gene Name:
mraY
Uniprot ID:
P0A6W3
Molecular weight:
39875
Reactions
UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol.
Protein Details
2. UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase
General function:
Involved in undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase activity
Specific function:
Cell wall formation. 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)
Gene Name:
murG
Uniprot ID:
P17443
Molecular weight:
37815
Reactions
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol.