Record Information
Version2.0
Creation Date2012-05-31 14:50:41 -0600
Update Date2015-06-03 17:20:18 -0600
Secondary Accession Numbers
  • ECMDB20560
Identification
Name:Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate
DescriptionUndecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate or C5PP GlcNAc is involved in ECA biosynthesis. It is a substrate for Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase. This enzyme catalyzes the transfer of the GlcNAc-1-phosphate moiety from UDP-GlcNAc onto the carrier lipid undecaprenyl phosphate (C55-P), yielding GlcNAc-pyrophosphoryl-undecaprenyl (GlcNAc-PP-C55). It is the first lipid-linked intermediate involved in enterobacterial common antigen (ECA) synthesis and an acceptor for the addition of subsequent sugars to complete the biosynthesis of O-antigen (PMID 1730666). GlcNAc-pyrophosphorylundecaprenol functions as the acceptor of mannose residues for the in vivo synthesis of O8 side chains in E. coli.(PMID 7514591). Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.
Structure
Thumb
Synonyms:
  • N-acetyl-D-glucosaminyldiphospho-undecaprenol
  • N-acetyl-D-glucosaminyldiphosphoundecaprenol
  • N-acetyl-glucosaminyl-pyrophosphorylundecaprenol
  • N-[4,5-dihydroxy-2-[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-undecaenoxy)phosphinoyl)oxy-phosphinoyl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
  • C55-PP-GlcNAc
  • Ditrans,polycis-undecaprenyl-N-acetyl-D-glucosaminyl diphosphate
  • Ditrans,polycis-undecaprenyl-N-acetyl-D-glucosaminyl diphosphoric acid
  • Glcnac-PP-lipid
  • Glcnac-pyrophosphorylundecaprenol
  • Lipid I
  • N-Acetyl-D-glucosaminyldiphospho-undecaprenol
  • N-Acetyl-D-glucosaminyldiphosphoundecaprenol
  • N-Acetyl-glucosaminyl-pyrophosphorylundecaprenol
  • N-[4,5-Dihydroxy-2-[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-undecaenoxy)phosphinoyl)oxy-phosphinoyl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
  • Prenyl-P-P-GlcNAc
  • Undecaprenyl diphospho N-acetyl-glucosamine
  • Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphate
  • Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphate
  • Undecaprenyl-n-acetyl-α-D-glucosaminyl-pyrophosphate
  • Undecaprenyl-n-acetyl-α-D-glucosaminyl-pyrophosphoric acid
  • Undecaprenyl-N-acetyl-a-D-glucosaminyl-pyrophosphate
  • Undecaprenyl-N-acetyl-a-D-glucosaminyl-pyrophosphoric acid
  • Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphoric acid
  • Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphate
  • Undecaprenyl-n-acetyl-D-glucosaminyl-pyrophosphoric acid
  • Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphoric acid
  • Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphate
  • Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphoric acid
Chemical Formula:C63H105NO12P2
Weight:Average: 1130.4548
Monoisotopic: 1129.711200853
InChI Key:NEVJGTXBHJNFAZ-UHFFFAOYSA-N
InChI:InChI=1S/C63H105NO12P2/c1-47(2)24-14-25-48(3)26-15-27-49(4)28-16-29-50(5)30-17-31-51(6)32-18-33-52(7)34-19-35-53(8)36-20-37-54(9)38-21-39-55(10)40-22-41-56(11)42-23-43-57(12)44-45-73-77(69,70)76-78(71,72)75-63-60(64-58(13)66)62(68)61(67)59(46-65)74-63/h24,26,28,30,32,34,36,38,40,42,44,59-63,65,67-68H,14-23,25,27,29,31,33,35,37,39,41,43,45-46H2,1-13H3,(H,64,66)(H,69,70)(H,71,72)
CAS number:Not Available
IUPAC Name:N-(4,5-dihydroxy-2-{[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}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid
Traditional IUPAC Name:N-[4,5-dihydroxy-2-({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)-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
SMILES:CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(=O)OC1OC(CO)C(O)C(O)C1N=C(C)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
  • Polyprenyl phospho carbohydrate
  • Bactoprenol diphosphate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Isoprenoid phosphate
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00039 g/LALOGPS
logP8.48ALOGPS
logP14.82ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)1.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area204.8 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity330.92 m³·mol⁻¹ChemAxon
Polarizability132.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Secondary Metabolites: enterobacterial common antigen biosynthesis 3PW002046 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • enterobacterial common antigen biosynthesis ECASYN-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-3621000901-6ff614f5acc94b6280c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0121000910-05f0454830cf4b971ea3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0121110900-1aecb86a3bd5b807a31cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0570-9400000004-0138b8e07cb3c1938f1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7925000203-a87f9fb6aa9386a53c00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-e4caa11e9b995ebfdc61View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
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
  • Rick, P. D., Hubbard, G. L., Barr, K. (1994). "Role of the rfe gene in the synthesis of the O8 antigen in Escherichia coli K-12." J Bacteriol 176:2877-2884. Pubmed: 7514591
  • Rick, P. D., Mayer, H., Neumeyer, B. A., Wolski, S., Bitter-Suermann, D. (1985). "Biosynthesis of enterobacterial common antigen." J Bacteriol 162:494-503. Pubmed: 3886625
  • Zheng, Y., Struck, D. K., Bernhardt, T. G., Young, R. (2008). "Genetic analysis of MraY inhibition by the phiX174 protein E." Genetics 180:1459-1466. Pubmed: 18791230
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID182
Kegg IDNot Available
ChemSpider ID177
Wikipedia IDNot Available
BioCyc IDACETYL-D-GLUCOSAMINYLDIPHOSPHO-UNDECAPRE
EcoCyc IDACETYL-D-GLUCOSAMINYLDIPHOSPHO-UNDECAPRE

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the transfer of the GlcNAc-1-phosphate moiety from UDP-GlcNAc onto the carrier lipid undecaprenyl phosphate (C55-P), yielding GlcNAc-pyrophosphoryl-undecaprenyl (GlcNAc-PP- C55). It is the first lipid-linked intermediate involved in enterobacterial common antigen (ECA) synthesis and an acceptor for the addition of subsequent sugars to complete the biosynthesis of O-antigen. The apparent affinity of WecA for the polyisoprenyl phosphate substrates increases with the polyisoprenyl chain length. WecA is unable to utilize dolichyl phosphate (Dol-P)
Gene Name:
wecA
Uniprot ID:
P0AC78
Molecular weight:
40957
Reactions
UDP-N-acetyl-D-glucosamine + di-trans,octa-cis-undecaprenyl phosphate = UMP + N-acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol.
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA (Lipid II), the second lipid-linked intermediate involved in ECA synthesis
Gene Name:
wecG
Uniprot ID:
P27836
Molecular weight:
27928
Reactions
UDP-ManNAcA + Und-PP-GlcNAc = UDP + Und-PP-GlcNAc-ManNAcA.