Record Information
Version2.0
Creation Date2012-07-30 14:55:16 -0600
Update Date2015-09-17 15:41:48 -0600
Secondary Accession Numbers
  • ECMDB21298
Identification
Name:Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate
DescriptionUndecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronateis an intermediate in enterobacterial common antigen (ECA) synthesis. It is a substrate for 4-alpha-L-fucosyltransferase (wecF) This enzyme catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA-Fuc4NAc (Lipid III), the third lipid-linked intermediate involved in ECA synthesis. Enterobacterial common antigen (ECA) is an outer membrane glycolipid similar to LPS that is 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:
  • C55-PP-GlcNAc-ManNAcA
  • Lipid II
  • ManNAcA-GlcNAc-PP-lipid
  • ManNAcA-GlcNAc-pyrophosphorylundecaprenol
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphate
  • Undecaprenyl n-acetyl-glucosaminyl-n-acetyl-mannosaminuronic acid pyrophosphoric acid
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphoric acid
  • Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate
  • Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronic acid
Chemical Formula:C71H116N2O18P2
Weight:Average: 1347.6309
Monoisotopic: 1346.769837942
InChI Key:IGGGNUSEBUZFTR-CDDUTUKUSA-N
InChI:InChI=1S/C71H116N2O18P2/c1-48(2)25-15-26-49(3)27-16-28-50(4)29-17-30-51(5)31-18-32-52(6)33-19-34-53(7)35-20-36-54(8)37-21-38-55(9)39-22-40-56(10)41-23-42-57(11)43-24-44-58(12)45-46-86-92(82,83)91-93(84,85)90-71-63(73-60(14)76)65(78)67(61(47-74)87-71)88-70-62(72-59(13)75)64(77)66(79)68(89-70)69(80)81/h25,27,29,31,33,35,37,39,41,43,45,61-68,70-71,74,77-79H,15-24,26,28,30,32,34,36,38,40,42,44,46-47H2,1-14H3,(H,72,75)(H,73,76)(H,80,81)(H,82,83)(H,84,85)/b49-27+,50-29+,51-31+,52-33+,53-35+,54-37+,55-39+,56-41+,57-43+,58-45+/t61-,62+,63-,64-,65-,66+,67-,68+,70-,71-/m1/s1
CAS number:Not Available
IUPAC Name:(2S,3S,4R,5S,6R)-3,4-dihydroxy-6-{[(2R,3S,4R,5R,6R)-4-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}-2-(hydroxymethyl)-5-[(1-oxidoethylidene)amino]oxan-3-yl]oxy}-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
Traditional IUPAC Name:(2S,3S,4R,5S,6R)-3,4-dihydroxy-6-{[(2R,3S,4R,5R,6R)-4-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}-2-(hydroxymethyl)-5-[(1-oxidoethylidene)amino]oxan-3-yl]oxy}-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
SMILES:OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@@H]1NC(=O)C
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP7.46ALOGPS
logP14.47ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area321.87 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity406.76 m³·mol⁻¹ChemAxon
Polarizability151.23 ųChemAxon
Number of Rings2ChemAxon
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 biosynthesisPW000959 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: enterobacterial common antigen biosynthesis 2PW002045 ThumbThumb?image type=greyscaleThumb?image type=simple
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, Positivesplash10-01ox-0009000000-1f3ff0dd99f358e14841View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0009000100-98367624b9acfda19b76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-3119100710-f9989d9a1302a391f394View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-2609000000-1b26b0e059d997c76b71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00y3-9201000000-b683817c4019f3260befView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08iv-9500000000-3d93a55212f860b03c8aView in MoNA
References
References:
  • Gerard, F., Brooks, M. A., Barreteau, H., Touze, T., Graille, M., Bouhss, A., Blanot, D., van Tilbeurgh, H., Mengin-Lecreulx, D. (2011). "X-ray structure and site-directed mutagenesis analysis of the Escherichia coli colicin M immunity protein." J Bacteriol 193:205-214. Pubmed: 21037007
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61495
HMDB IDNot Available
Pubchem Compound ID44229184
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDC55-PP-GLCNAC-MANNACA
EcoCyc IDC55-PP-GLCNAC-MANNACA

Enzymes

General function:
Involved in fucosyltransferase activity
Specific function:
Catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA-Fuc4NAc (Lipid III), the third lipid-linked intermediate involved in ECA synthesis
Gene Name:
wecF
Uniprot ID:
P56258
Molecular weight:
40639
Reactions
TDP-Fuc4NAc + Und-PP-GlcNAc-ManNAcA = TDP + Und-PP-GlcNAc-ManNAcA-Fuc4NAc.
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.