ECMDB: UDP-D-Galacto-1,4-furanose (ECMDB04165) (M2MDB000645)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (70)

Record Information

Version

2.0

Creation Date

2012-05-31 14:06:58 -0600

Update Date

2015-06-03 15:54:49 -0600

Secondary Accession Numbers

ECMDB04165

Identification

Name:

UDP-D-Galacto-1,4-furanose

Description

UDP-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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine 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 Framework

Aromatic 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:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	24.6 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-4.6	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	295.03 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	106.78 m³·mol⁻¹	ChemAxon
Polarizability	46.19 Å³	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:

Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + UDP-D-Galacto-1,4-furanose > Galactofuranosyl-glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Hydrogen ion + Uridine 5'-diphosphate
Uridine diphosphategalactose > UDP-D-Galacto-1,4-furanose
Uridine diphosphategalactose <> UDP-D-Galacto-1,4-furanose
octyl alpha-D-glucopyranoside + UDP-D-Galacto-1,4-furanose Hydrogen ion + octyl beta-1,6-D-galactofuranosyl-alpha-D-glucopyranoside + Uridine 5'-diphosphate
UDP-α-D-galactose <> UDP-D-Galacto-1,4-furanose

SMPDB Pathways:

Galactose metabolism	PW000821
Lipopolysaccharide biosynthesis	PW000831
O-antigen building blocks biosynthesis	PW002089

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
Galactose metabolism ec00052
Lipopolysaccharide biosynthesis ec00540

EcoCyc Pathways:

O-antigen building blocks biosynthesis (E. coli) OANTIGEN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901110000-55b06bcaae49b03172a4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3911000000-31030978cb90646bedd0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-7900000000-c844ec7d281f230bdc1d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-5601390000-ef8f9cd33d9e87228e3b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06r6-8906010000-614feaf3d5c0a9685553	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvl-4901000000-d1cbf9c7768d56984ad6	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
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

Links

External Links:

Resource	Link
CHEBI ID	18251
HMDB ID	Not Available
Pubchem Compound ID	25244316
Kegg ID	C03733
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	UDP-D-GALACTO-14-FURANOSE
EcoCyc ID	UDP-D-GALACTO-14-FURANOSE

Enzymes

Protein Details

1. UDP-galactopyranose mutase

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.

Protein Details

2. Uncharacterized protein yefG

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

UDP-D-Galacto-1,4-furanose (ECMDB04165) (M2MDB000645)

Structure for #<Compound:0xadacb4c8>

Enzymes

Reactions