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Record Information
Version	2.0
Creation Date	2012-05-31 14:53:23 -0600
Update Date	2015-06-03 17:20:23 -0600
Secondary Accession Numbers	ECMDB20612
Identification
Name:	dTDP-D-Fucosamine
Description	dTDP-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab049b28> Close
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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine nucleotide sugars
Direct Parent	Pyrimidine nucleotide sugars
Alternative Parents	Pentose phosphates Organic pyrophosphates Monosaccharide phosphates Pyrimidones Monoalkyl phosphates Hydroxypyrimidines Aminosaccharides Oxanes Hydropyrimidines Tetrahydrofurans Heteroaromatic compounds Secondary alcohols 1,2-aminoalcohols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
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 Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 14.3 g/L ALOGPS logP -1.6 ALOGPS logP -3.6 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) 8.9 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 260.36 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 109.74 m³·mol⁻¹ ChemAxon Polarizability 46.89 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 3 PW002046
KEGG Pathways:	Not Available
EcoCyc Pathways:	enterobacterial common antigen biosynthesis ECASYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_34) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-22af95e13d015d0d9536 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-3911000000-8a9547ed00c5493d6a82 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004i-4900000000-75793e707d76dba12315 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f7a-9602470000-33afad6078f3732b8310 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0fbi-8904000000-c405ac366b425f2c8e05 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a6u-5901000000-464e304ac642b4877a41 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 25202013 Kegg ID C04346 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID TDP-D-FUCOSAMINE EcoCyc ID TDP-D-FUCOSAMINE

Enzymes