dTDP-D-Fucosamine (ECMDB20612) (M2MDB001411)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-05-31 14:53:23 -0600
Update Date2015-06-03 17:20:23 -0600
Secondary Accession Numbers
  • ECMDB20612
Identification
Name:dTDP-D-Fucosamine
DescriptiondTDP-D-fucosamine 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. This compound is involved in the synthesis of enterobacterial common antigen (ECA) synthesis through the reaction: dTDP-alpha-D-fucosamine + acetyl-CoA <=> dTDP-4-acetamido-4,6-dideoxy-D-galactose + coenzyme A + H+. Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae (including E. coli). The carbohydrate portion of this glycolipid 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
MOLSDFPDBSMILESInChI
Synonyms:
  • DTDP-4-amino-4,6-dideoxy-α-D-galactose
  • dTDP-4-amino-4,6-Dideoxy-a-D-galactose
  • DTDP-4-Amino-4,6-dideoxy-alpha-D-galactose
  • DTDP-4-Amino-4,6-dideoxy-D-galactose
  • dTDP-4-amino-4,6-Dideoxy-α-D-galactose
  • TDP-D-Fucosamine
  • TDP-Fucn
  • TDP-Fucosamine
Chemical Formula:C16H27N3O14P2
Weight:Average: 547.3448
Monoisotopic: 547.096825611
InChI Key:UIVJXHWSIFBBCY-DBRXDORISA-N
InChI:InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/t7-,8?,9?,10?,11+,12+,13-,15-/m1/s1
CAS number:Not Available
IUPAC Name:[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid
Traditional IUPAC Name:{[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid
SMILES:[H]C1(O)CC([H])(OC1([H])COP(O)(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(C)[C@]([H])(N)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C(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
  • Pentose phosphate
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Amino saccharide
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-1.6ALOGPS
logP-3.6ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area260.36 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity109.74 m³·mol⁻¹ChemAxon
Polarizability46.89 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Acetyl-CoA + dTDP-D-Fucosamine > Coenzyme A + dTDP-4-Acetamido-4,6-dideoxy-D-galactose + Hydrogen ion
4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate > alpha-Ketoglutarate + dTDP-D-Fucosamine
4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate <> dTDP-D-Fucosamine + Oxoglutaric acid
Acetyl-CoA + dTDP-D-Fucosamine <> Coenzyme A + dTDP-4-acetamido-4,6-dideoxy-alpha-D-galactose
dTDP-D-Fucosamine + alpha-Ketoglutarate <> 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate
dTDP-4-dehydro-6-deoxy-D-glucose + L-Glutamate > Oxoglutaric acid + dTDP-D-Fucosamine
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_34) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-22af95e13d015d0d9536View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3911000000-8a9547ed00c5493d6a82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4900000000-75793e707d76dba12315View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f7a-9602470000-33afad6078f3732b8310View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbi-8904000000-c405ac366b425f2c8e05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-5901000000-464e304ac642b4877a41View 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
  • 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
  • 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 IDNot Available
HMDB IDNot Available
Pubchem Compound ID25202013
Kegg IDC04346
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDTDP-D-FUCOSAMINE
EcoCyc IDTDP-D-FUCOSAMINE

Enzymes

Protein Details
1. Lipopolysaccharide biosynthesis protein rffC
General function:
Involved in protein binding
Specific function:
Transaminase converting thymidine diphosphate(TDP)-4- keto-6-deoxy-D-glucose to TDP-4-amino-4,6-dideoxy-D-galactose, the immediate precursor of the ECA sugar TDP-Fuc4NAc
Gene Name:
rffC
Uniprot ID:
P27832
Molecular weight:
24220
Protein Details
2. Lipopolysaccharide biosynthesis protein rffA
General function:
Involved in catalytic activity
Specific function:
Involved in ECA elongation
Gene Name:
rffA
Uniprot ID:
P27833
Molecular weight:
41901