Record Information
Version2.0
Creation Date2012-05-31 14:35:42 -0600
Update Date2015-06-03 17:19:39 -0600
Secondary Accession Numbers
  • ECMDB20257
Identification
Name:N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol
DescriptionN-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol is an intermediate in peptidoglycan synthesis. It is a substrate for the enzyme undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase (murG). Peptidoglycan can be described as a fisherman's net that encloses bacteria. The mesh of the net is made of two segments of parallel, somewhat 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 very 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 lengthof 10 to 65 disaccharide units (depending on the organism). The peptidoglycan synthesis pathway starts in 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.Glycosyltransferase MurG catalyses the transfer of N-acetyl-d-glucosamine to lipid intermediate I on the bacterial peptidoglycan biosynthesis pathway, and is a target for development of new antibacterial agents. (PMID 20226679)
Structure
Thumb
Synonyms:
  • N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptane-D-alanyl-D-alanine-diphosphoundecaprenol
  • Lipid intermediate I
  • Lipid intermediic acid I
  • N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptane-D-alanyl-D-alanine-diphosphoundecaprenol
  • Undecaprenyl-pyrophosphoryl-murnac-pentapeptide
Chemical Formula:C87H143N7O23P2
Weight:Average: 1717.0469
Monoisotopic: 1715.971056941
InChI Key:PNWZQTONLRRPST-OPZGOLSISA-N
InChI:InChI=1S/C87H143N7O23P2/c1-56(2)29-18-30-57(3)31-19-32-58(4)33-20-34-59(5)35-21-36-60(6)37-22-38-61(7)39-23-40-62(8)41-24-42-63(9)43-25-44-64(10)45-26-46-65(11)47-27-48-66(12)53-54-113-118(109,110)117-119(111,112)116-87-77(92-71(17)96)79(78(98)75(55-95)115-87)114-70(16)82(101)89-68(14)81(100)94-74(86(107)108)51-52-76(97)93-73(50-28-49-72(88)85(105)106)83(102)90-67(13)80(99)91-69(15)84(103)104/h29,31,33,35,37,39,41,43,45,47,53,67-70,72-75,77-79,87,95,98H,18-28,30,32,34,36,38,40,42,44,46,48-52,54-55,88H2,1-17H3,(H,89,101)(H,90,102)(H,91,99)(H,92,96)(H,93,97)(H,94,100)(H,103,104)(H,105,106)(H,107,108)(H,109,110)(H,111,112)/t67-,68+,69-,70-,72-,73+,74-,75-,77-,78-,79-,87+/m1/s1
CAS number:Not Available
IUPAC Name:(2R,6S)-2-amino-6-{[(4R)-4-carboxy-1-hydroxy-4-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6S)-3-hydroxy-6-{[hydroxy({hydroxy[(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}butylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid
Traditional IUPAC Name:(2R,6S)-2-amino-6-{[(4R)-4-carboxy-1-hydroxy-4-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6S)-3-hydroxy-6-({hydroxy[hydroxy(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]oxyphosphoryl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid
SMILES:[H][C@@](N)(CCC[C@]([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OP(O)(=O)OP(O)(=O)OCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)[C@]1([H])N=C(C)O)C(O)=O)C(O)=N[C@]([H])(C)C(O)=N[C@]([H])(C)C(O)=O)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
  • D-alpha-amino acid
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Isoprenoid phosphate
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Monosaccharide
  • 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:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP3.71ALOGPS
logP16.7ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area494.67 ŲChemAxon
Rotatable Bond Count60ChemAxon
Refractivity469.28 m³·mol⁻¹ChemAxon
Polarizability191.19 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1011139200-a5086b1fa04a83dc0d2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3130033911-ab862a3d1358e36e1757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001d-9333332400-1bd354ac67fc3da0fbdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06vj-3000039507-bfb6f7440faf705b9965View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-3300018109-4bce894814e4eb3aa402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-6910002002-df1a7b3aba2e08f6af47View in MoNA
References
References:
  • 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
  • Trunkfield, A. E., Gurcha, S. S., Besra, G. S., Bugg, T. D. (2010). "Inhibition of Escherichia coli glycosyltransferase MurG and Mycobacterium tuberculosis Gal transferase by uridine-linked transition state mimics." Bioorg Med Chem 18:2651-2663. Pubmed: 20226679
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25200588
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDC5
EcoCyc IDC5

Enzymes

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.
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.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022