Record Information
Version2.0
Creation Date2012-07-30 14:55:15 -0600
Update Date2015-09-17 15:41:48 -0600
Secondary Accession Numbers
  • ECMDB21297
Identification
Name:Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose
DescriptionUndecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose is 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:
  • a-D-FucNAc4-(1Right4)-b-D-mannaca-(1Right4)-D-glcnac-undecaprenyl diphosphate
  • a-D-FucNAc4-(1Right4)-b-D-mannaca-(1Right4)-D-glcnac-undecaprenyl diphosphoric acid
  • Alpha-D-FucNAc4-(1right4)-beta-D-ManNAcA-(1right4)-D-GlcNAc-undecaprenyl diphosphate
  • alpha-D-FucNAc4-(1Right4)-beta-D-mannaca-(1Right4)-D-glcnac-undecaprenyl diphosphoric acid
  • C55-PP-GlcNAc-ManNAcA-Fuc4NAc
  • Lipid III
  • ManNAcA-GlcNAc-Fuc4NAc-PP-lipid
  • ManNAcA-GlcNAc-Fuc4NAc-pyrophosphorylundecaprenol
  • N-Acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose undecaprenyl pyrophosphate(3)
  • N-Acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid-4-acetamido-4,6-dideoxy-D-galactose undecaprenyl pyrophosphoric acid(3)
  • Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose
  • Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronic acid-N-acetamido-4,6-dideoxy-D-galactose
  • α-D-FucNAc4-(1Right4)-β-D-mannaca-(1Right4)-D-glcnac-undecaprenyl diphosphate
  • α-D-FucNAc4-(1Right4)-β-D-mannaca-(1Right4)-D-glcnac-undecaprenyl diphosphoric acid
Chemical Formula:C79H129N3O22P2
Weight:Average: 1534.824
Monoisotopic: 1533.854295851
InChI Key:PSONHUYFSWYIME-JNYPHZTQSA-N
InChI:InChI=1S/C79H129N3O22P2/c1-50(2)27-17-28-51(3)29-18-30-52(4)31-19-32-53(5)33-20-34-54(6)35-21-36-55(7)37-22-38-56(8)39-23-40-57(9)41-24-42-58(10)43-25-44-59(11)45-26-46-60(12)47-48-97-105(93,94)104-106(95,96)103-78-68(82-64(16)86)70(88)73(65(49-83)99-78)100-77-67(81-63(15)85)71(89)74(75(102-77)76(91)92)101-79-72(90)69(87)66(61(13)98-79)80-62(14)84/h27,29,31,33,35,37,39,41,43,45,47,61,65-75,77-79,83,87-90H,17-26,28,30,32,34,36,38,40,42,44,46,48-49H2,1-16H3,(H,80,84)(H,81,85)(H,82,86)(H,91,92)(H,93,94)(H,95,96)/b51-29+,52-31+,53-33+,54-35+,55-37+,56-39+,57-41+,58-43+,59-45+,60-47+/t61-,65-,66?,67+,68-,69+,70-,71-,72-,73-,74+,75+,77-,78-,79-/m1/s1
CAS number:Not Available
IUPAC Name:N-[(2R,3R,4R,5S,6R)-5-{[(2R,3S,4R,5S,6S)-6-carboxy-5-{[(2R,3R,4S,5R,6R)-3,4-dihydroxy-6-methyl-5-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}-4-hydroxy-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}-4-hydroxy-2-{[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}-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidate
Traditional IUPAC Name:N-[(2R,3R,4R,5S,6R)-5-{[(2R,3S,4R,5S,6S)-6-carboxy-5-{[(2R,3R,4S,5R,6R)-3,4-dihydroxy-6-methyl-5-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}-4-hydroxy-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}-4-hydroxy-2-{[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}-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidate
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]2O[C@H](C)C(NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1NC(=O)C
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
  • Oligosaccharide phosphate
  • Polyprenyl monophosphate
  • Oligosaccharide
  • Polyprenyl phosphate skeleton
  • N-acyl-alpha-hexosamine
  • O-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • 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 Solubility0.0028 g/LALOGPS
logP7ALOGPS
logP14.28ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area393.15 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity448.97 m³·mol⁻¹ChemAxon
Polarizability170.08 ųChemAxon
Number of Rings3ChemAxon
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:Not Available
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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61496
HMDB IDNot Available
Pubchem Compound ID44229215
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDC55-PP-GLCNAC-MANNACA-FUC4NAC
EcoCyc IDC55-PP-GLCNAC-MANNACA-FUC4NAC

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 lipopolysaccharide biosynthetic process
Specific function:
Specific function unknown
Gene Name:
wzzE
Uniprot ID:
P0AG00
Molecular weight:
39489
General function:
Not Available
Specific function:
Could be involved in ECA polysaccharide chain elongation
Gene Name:
wzyE
Uniprot ID:
P27835
Molecular weight:
51517

Transporters

General function:
Involved in polysaccharide biosynthetic process
Specific function:
Specific function unknown
Gene Name:
wzxE
Uniprot ID:
P0AAA7
Molecular weight:
44959