Record Information
Version2.0
Creation Date2012-05-31 10:25:43 -0600
Update Date2015-09-13 12:56:07 -0600
Secondary Accession Numbers
  • ECMDB00290
Identification
Name:Uridine diphosphate-N-acetylglucosamine
DescriptionUridine diphosphate N-acetylglucosamine or UDP-GlcNAc is a nucleotide sugar and a coenzyme in metabolism. It is used by glycosyltransferases to transfer N-acetylglucosamine residues to substrates. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. Specifically, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is UDP-GlcNAc, which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.
Structure
Thumb
Synonyms:
  • N-[2-[[[5-[(2,4-Dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
  • UDP-α-N-acetyl-D-glucosamine
  • UDP-α-n-acetyl-D-glucosamine
  • UDP-2-acetamido-2-deoxy-α-D-glucose
  • UDP-2-acetamido-2-Deoxy-a-D-glucose
  • UDP-2-Acetamido-2-deoxy-alpha-D-glucose
  • UDP-2-acetamido-2-Deoxy-α-D-glucose
  • UDP-N-acetyl-D-glucosamine
  • UDP-N-acetyl-glucosamine
  • UDP-a-D-N-Acetylglucosamine
  • UDP-a-delta-N-Acetylglucosamine
  • UDP-a-N-Acetyl-D-glucosamine
  • UDP-a-δ-N-Acetylglucosamine
  • UDP-Acetyl-D-glucosamine
  • UDP-Acetyl-delta-glucosamine
  • UDP-Acetyl-δ-glucosamine
  • UDP-Acetylglucosamine
  • UDP-alpha-D-N-Acetylglucosamine
  • UDP-alpha-delta-N-Acetylglucosamine
  • UDP-alpha-N-Acetyl-D-glucosamine
  • UDP-GlcNAc
  • UDP-N-Acetyl-D-glucosamine
  • UDP-N-Acetyl-delta-glucosamine
  • UDP-N-Acetyl-glucosamine
  • UDP-N-Acetyl-δ-glucosamine
  • UDP-N-Acetylglucosamine
  • UDP-α-D-N-Acetylglucosamine
  • UDP-α-N-Acetyl-D-glucosamine
  • UDP-α-δ-N-Acetylglucosamine
  • UPPAG
  • Uridine 5'-Diphospho-N-Acetlyglucosamine
  • Uridine 5'-diphospho-N-acetylglucosamine
  • Uridine diphosphate N-acetylglucosamine
  • Uridine diphosphate N-acetyl-D-glucosamine
  • Uridine diphosphate N-acetyl-delta-glucosamine
  • Uridine diphosphate N-acetyl-δ-glucosamine
  • Uridine diphosphate N-acetylglucosamine
  • Uridine diphospho-2-acetamido-2-deoxy-D-glucose
  • Uridine diphospho-2-acetamido-2-deoxy-delta-glucose
  • Uridine diphospho-2-acetamido-2-deoxy-δ-glucose
  • Uridine diphospho-N-acetyl-D-glucosamine
  • Uridine diphospho-N-acetyl-delta-glucosamine
  • Uridine diphospho-N-acetyl-δ-glucosamine
  • Uridine diphospho-N-acetylglucosamine
  • Uridine diphosphoacetylglucosamine
  • Uridine diphosphoric acid N-acetyl-D-glucosamine
  • Uridine diphosphoric acid N-acetyl-delta-glucosamine
  • Uridine diphosphoric acid N-acetyl-δ-glucosamine
  • Uridine diphosphoric acid n-acetylglucosamine
  • Uridine diphosphoric acid N-acetylglucosamine
  • Uridine diphosphoric acid-N-acetylglucosamine
  • Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-a-delta-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-a-δ-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-α-D-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-α-δ-glucopyranosyl ester
  • Uridine pyrophosphoacetylglucosamine
  • Uridine pyrophosphoric acid 2-acetamido-2-deoxy-a-D-glucopyranosyl ester
  • Uridine pyrophosphoric acid 2-acetamido-2-deoxy-a-delta-glucopyranosyl ester
  • Uridine pyrophosphoric acid 2-acetamido-2-deoxy-a-δ-glucopyranosyl ester
  • Uridine pyrophosphoric acid 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester
  • Uridine pyrophosphoric acid 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester
  • Uridine pyrophosphoric acid 2-acetamido-2-deoxy-α-D-glucopyranosyl ester
  • Uridine pyrophosphoric acid 2-acetamido-2-deoxy-α-δ-glucopyranosyl ester
  • [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate
  • [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid
Chemical Formula:C17H27N3O17P2
Weight:Average: 607.3537
Monoisotopic: 607.081569477
InChI Key:LFTYTUAZOPRMMI-CFRASDGPSA-N
InChI:InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
CAS number:528-04-1
IUPAC Name:[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Name:udp-N-acetyl-α-D-glucosamine
SMILES:CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Acetamide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility11.4 g/LALOGPS
logP-1.4ALOGPS
logP-5.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.41 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.56 m³·mol⁻¹ChemAxon
Polarizability50.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + Uridine diphosphate-N-acetylglucosamine <> acyl carrier protein + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine
Uridine diphosphate-N-acetylglucosamine + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine > Hydrogen ion + Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-diphosphate
Water + Uridine diphosphate-N-acetylglucosamine > N-Acetyl-glucosamine 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
N-Acetyl-glucosamine 1-phosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Uridine diphosphate-N-acetylglucosamine + Undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate
Uridine diphosphate-N-acetylglucosamine <> UDP-N-Acetyl-D-mannosamine
Uridine diphosphate-N-acetylglucosamine + Water <> N-Acetylmannosamine + Uridine 5'-diphosphate
Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
(3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + Uridine diphosphate-N-acetylglucosamine + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] <> Acyl-carrier protein + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine + Acyl-carrier protein
Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-diphosphate
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
Uridine diphosphate-N-acetylglucosamine + Di-trans,poly-cis-undecaprenyl phosphate <> N-Acetyl-D-glucosaminyldiphosphoundecaprenol + Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol
Uridine diphosphate-N-acetylglucosamine poly-&beta;-1,6-N-acetyl-D-glucosamine + Uridine 5'-diphosphate
a lipopolysaccharide + Uridine diphosphate-N-acetylglucosamine a <i>N</i>-acetyl-D-glucosaminyl-lipopolysaccharide + Uridine 5'-diphosphate
Di-trans,poly-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + Uridine 5'-monophosphate
N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol + Uridine diphosphate-N-acetylglucosamine <> Hydrogen ion + N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine + Uridine 5'-diphosphate
Hydrogen ion + <i>N</i>-acetyl-&alpha;-D-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate
Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + Phosphate
Uridine triphosphate + N-acetyl-alpha-D-glucosamine 1-phosphate > Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
(R)-3-hydroxytetradecanoyl-[acyl-carrier-protein] + Uridine diphosphate-N-acetylglucosamine > [acyl-carrier-protein] + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine
Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine > Inorganic phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
Uridine diphosphate-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > Uridine 5'-diphosphate + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
Uridine diphosphate-N-acetylglucosamine + LPS (1-O-antigen) > Uridine 5'-diphosphate + N-acetyl-D-glucosaminyllipopolysaccharide
Uridine diphosphate-N-acetylglucosamine + di-trans,octa-cis-undecaprenyl phosphate > Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol
Uridine diphosphate-N-acetylglucosamine > UDP-N-Acetyl-D-mannosamine
Uridine diphosphate-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol <> Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Uridine diphosphate-N-acetylglucosamine + LPS (1-O-antigen) <> Uridine 5'-diphosphate
Uridine diphosphate-N-acetylglucosamine + (3R)-3-hydroxymyristoyl-[acp] > a holo-[acyl-carrier protein] + UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-α-D-glucosamine
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + Hydrogen ion + N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate
Uridine diphosphate-N-acetylglucosamine <> UDP-N-acetyl-D-mannosamine + UDP-N-Acetyl-D-mannosamine
Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > Phosphate + UDP-N-acetyl-α-D-glucosamine-enolpyruvate
Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine diphosphate-N-acetylglucosamine + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine > Uridine 5'-diphosphate + Hydrogen ion + lipid II(A) + Uridine 5'-diphosphate
di-trans,octa-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine > Uridine 5'-monophosphate + N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol
N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol + Uridine diphosphate-N-acetylglucosamine > Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-diphosphate + Hydrogen ion
Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
More...

SMPDB Pathways:
1,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPW002064 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
O-antigen building blocks biosynthesisPW002089 ThumbThumb?image type=greyscaleThumb?image type=simple
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
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
9240± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
4110± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
2400± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
542± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (n TMS)splash10-00di-9620000000-18841b4db9b69a91db36View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-18841b4db9b69a91db36View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-5924660000-c11cc7fa21a050c0f373View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-5501619000-8584f57aecb61fc3e5b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-5543009000-8a176d160a1f074ab319View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-05cr-4796000000-6c09aa3a2dac66281973View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-5543009000-8a176d160a1f074ab319View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05cr-4796000000-6c09aa3a2dac66281973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910020000-b4f448790a5adc1b2231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-b1ea97b129b6c701887eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-af36b4483c7d5529ce86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pc-9801421000-87db24d9515a2033d9b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-9605020000-323a53bc8a8e293636d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-aee8e2f7d665fa10b3b1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
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  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Jamieson JC, Kaplan HA, Woloski BM, Hellman M, Ham K: Glycoprotein biosynthesis during the acute-phase response to inflammation. Can J Biochem Cell Biol. 1983 Sep;61(9):1041-8. Pubmed: 6627106
  • 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
  • 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
  • Kim CH: Increased expression of N-acetylglucosaminyltransferase-V in human hepatoma cells by retinoic acid and 1alpha,25-dihydroxyvitamin D3. Int J Biochem Cell Biol. 2004 Nov;36(11):2307-19. Pubmed: 15313475
  • Kobayashi T, Sleeman JE, Coughtrie MW, Burchell B: Molecular and functional characterization of microsomal UDP-glucuronic acid uptake by members of the nucleotide sugar transporter (NST) family. Biochem J. 2006 Dec 1;400(2):281-9. Pubmed: 16965264
  • Love DC, Hanover JA: The hexosamine signaling pathway: deciphering the "O-GlcNAc code". Sci STKE. 2005 Nov 29;2005(312):re13. Pubmed: 16317114
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Wells L, Vosseller K, Hart GW: A role for N-acetylglucosamine as a nutrient sensor and mediator of insulin resistance. Cell Mol Life Sci. 2003 Feb;60(2):222-8. Pubmed: 12678487
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Takenouchi, Kenji; Ishige, Kazuya; Midorikawa, Yuichiro; Okuyama, Kiyoshi; Hamamoto, Tomoki; Noguchi, Toshitada. Process for producing uridine diphosphate-N-acetylglucosamine. PCT Int. Appl. (1999), 38 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16264
HMDB IDHMDB00290
Pubchem Compound ID10705
Kegg IDC00043
ChemSpider ID393240
WikipediaUDP-N-acetylglucosamine
BioCyc IDUDP-N-ACETYL-D-GLUCOSAMINE
EcoCyc IDUDP-N-ACETYL-D-GLUCOSAMINE
Ligand ExpoUD1

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in transferase activity
Specific function:
Involved in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell
Gene Name:
lpxA
Uniprot ID:
P0A722
Molecular weight:
28080
Reactions
(R)-3-hydroxytetradecanoyl-[acyl-carrier-protein] + UDP-N-acetylglucosamine = [acyl-carrier-protein] + UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine.
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Cell wall formation. Adds enolpyruvyl to UDP-N- acetylglucosamine. Target for the antibiotic phosphomycin
Gene Name:
murA
Uniprot ID:
P0A749
Molecular weight:
44817
Reactions
Phosphoenolpyruvate + UDP-N-acetyl-D-glucosamine = phosphate + UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine.
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 magnesium ion binding
Specific function:
Catalyzes the last two sequential reactions in the de novo biosynthetic pathway for UDP-GlcNAc. Responsible for the acetylation of Glc-N-1-P to give GlcNAc-1-P and for the uridyl transfer from UTP to GlcNAc-1-P which produces UDP-GlcNAc
Gene Name:
glmU
Uniprot ID:
P0ACC7
Molecular weight:
49190
Reactions
Acetyl-CoA + alpha-D-glucosamine 1-phosphate = CoA + N-acetyl-alpha-D-glucosamine 1-phosphate.
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine.
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 UDP-N-acetylglucosamine 2-epimerase activity
Specific function:
Catalyzes the reversible epimerization at C-2 of UDP-N- acetylglucosamine (UDP-GlcNAc) and thereby provides bacteria with UDP-N-acetylmannosamine (UDP-ManNAc), the activated donor of ManNAc residues. Also involved in bacteriophage N4 adsorption
Gene Name:
wecB
Uniprot ID:
P27828
Molecular weight:
42244
Reactions
UDP-N-acetyl-D-glucosamine = UDP-N-acetyl-D-mannosamine.
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Adds the terminal N-acetyl-D-glucosamine group on the glucose(II) group of LPS
Gene Name:
waaU
Uniprot ID:
P27242
Molecular weight:
41729
Reactions
UDP-N-acetyl-D-glucosamine + lipopolysaccharide = UDP + N-acetyl-D-glucosaminyllipopolysaccharide.
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Uniprot ID:
P0A6A8
Molecular weight:
8640

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368