Record Information
Version2.0
Creation Date2012-05-31 14:06:58 -0600
Update Date2015-06-03 15:54:49 -0600
Secondary Accession Numbers
  • ECMDB04165
Identification
Name:UDP-D-Galacto-1,4-furanose
DescriptionUDP-D-galacto-1,4-furanose is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphogalactofuranose (UDP-Galf) is the precursor of the d-galactofuranose (Galf) residues found in bacterial and parasitic cell walls, including those of many pathogens, such as Mycobacterium tuberculosis and Trypanosoma cruzi. (PMID 11573090) UDP-galactopyranose mutase (UGM) is a flavin-containing enzyme that catalyzes the conversion of UDP-galactopyranose to UDP-galactofuranose, the precursor of galactofuranose, which is an important cell wall component in Aspergillus fumigatus and other pathogenic microbes. (PMID 20615386)
Structure
Thumb
Synonyms:
  • UDP-a-D-galacto-1,4-Furanose
  • UDP-a-D-Galactofuranose
  • UDP-alpha-D-galacto-1,4-furanose
  • UDP-alpha-D-galactofuranose
  • UDP-D-galacto-1,4-furanose
  • UDP-Galf
  • UDP-galactofuranose
  • UDP-Galf
  • UDP-α-D-galacto-1,4-Furanose
  • UDP-α-D-Galactofuranose
Chemical Formula:C15H24N2O17P2
Weight:Average: 566.3018
Monoisotopic: 566.055020376
InChI Key:ZQLQOXLUCGXKHS-SIAUPFDVSA-N
InChI:InChI=1S/C15H24N2O17P2/c18-3-5(19)12-9(22)11(24)14(32-12)33-36(28,29)34-35(26,27)30-4-6-8(21)10(23)13(31-6)17-2-1-7(20)16-15(17)25/h1-2,5-6,8-14,18-19,21-24H,3-4H2,(H,26,27)(H,28,29)(H,16,20,25)/t5-,6-,8-,9-,10-,11-,12+,13-,14-/m1/s1
CAS number:638-23-3
IUPAC Name:[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy})phosphinic acid
Traditional IUPAC Name:udp-D-galacto-1,4-furanose
SMILES:[H][C@@](O)(CO)[C@]1([H])O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@@]1([H])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
  • Sugar acid
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Acetamide
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Urea
  • Lactam
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine (CHEBI:68507 )
Physical Properties
State:Solid
Charge:-2
Melting point:206 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility24.6 g/LALOGPS
logP-1.3ALOGPS
logP-4.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area295.03 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity106.78 m³·mol⁻¹ChemAxon
Polarizability46.19 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactose metabolismPW000821 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
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
  • Galactose metabolism ec00052
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_15) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-55b06bcaae49b03172a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-31030978cb90646bedd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7900000000-c844ec7d281f230bdc1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5601390000-ef8f9cd33d9e87228e3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06r6-8906010000-614feaf3d5c0a9685553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvl-4901000000-d1cbf9c7768d56984ad6View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Oppenheimer, M., Poulin, M. B., Lowary, T. L., Helm, R. F., Sobrado, P. (2010). "Characterization of recombinant UDP-galactopyranose mutase from Aspergillus fumigatus." Arch Biochem Biophys 502:31-38. Pubmed: 20615386
  • Sanders, D. A., Staines, A. G., McMahon, S. A., McNeil, M. R., Whitfield, C., Naismith, J. H. (2001). "UDP-galactopyranose mutase has a novel structure and mechanism." Nat Struct Biol 8:858-863. Pubmed: 11573090
  • 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:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18251
HMDB IDNot Available
Pubchem Compound ID25244316
Kegg IDC03733
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDUDP-D-GALACTO-14-FURANOSE
EcoCyc IDUDP-D-GALACTO-14-FURANOSE

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Involved in the conversion of UDP-GalP into UDP-GalF through a 2-keto intermediate
Gene Name:
glf
Uniprot ID:
P37747
Molecular weight:
42966
Reactions
UDP-D-galactopyranose = UDP-D-galacto-1,4-furanose.
General function:
Involved in lipopolysaccharide-1,6-galactosyltransferas
Specific function:
May be a glycosyltransferase involved in the transfer of UDP-GalF to the lipopolysaccharide
Gene Name:
yefG
Uniprot ID:
P37749
Molecular weight:
37757