UDP-β-L-threo-pentapyranos-4-ulose (PAMDB006357)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB006357
Identification
Name: UDP-β-L-threo-pentapyranos-4-ulose
Description:UDP-beta-L-threo-pentapyranos-4-ulose is an intermediate in the polymixin resistance pathway. It is a substrate for the enzyme UDP-4-amino-4-deoxy-L-arabinose aminotransferase which catalyzes the reaction UDP-4-amino-4-deoxy-beta-L-arabinopyranose + 2-oxoglutarate = UDP-beta-L-threo-pentapyranos-4-ulose + L-glutamate. Some Gram-negative bacteria, specifically Salmonella typhimurium and Pseudomonas aeruginosa, can become resistant to polymyxin by the modification of their lipid A structure via the attachment of 4-amino-4-deoxy-L-arabinopyranose (L-Ara4N) groups to one or more phosphate groups. This addition causes an absolute increase in lipid A charge, thus lowering the affinity of positively charged polymyxins.
Structure
Thumb
Synonyms:Not Available
Chemical Formula: C14H20N2O16P2
Average Molecular Weight: 534.26
Monoisotopic Molecular Weight: 534.028806568
InChI Key: URJZIQLTPCJVMW-QNSCKLTRSA-N
InChI:InChI=1S/C14H20N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,6,8-13,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t6-,8+,9-,10-,11-,12-,13-/m1/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2OCC(=O)[C@H](O)[C@H]2O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
UDP-Glucuronic acid + NAD > Carbon dioxide + NADH + UDP-β-L-threo-pentapyranos-4-ulose
UDP-β-L-threo-pentapyranos-4-ulose + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IIIPW000895 Pw000895Pw000895 greyscalePw000895 simple
polymyxin resistancePW002052 Pw002052Pw002052 greyscalePw002052 simple
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
UDP-Glucuronic acid + NAD > Carbon dioxide + NADH + UDP-β-L-threo-pentapyranos-4-ulose
UDP-β-L-threo-pentapyranos-4-ulose + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-2a9cc7795df7c73bd5a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3910000000-5be40f633892a3da5ec7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-17d35afaa6d28f5fad3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gwf-8903680000-b8f22688f6b7a8e6331aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-8923010000-832a49f2363fe2cd64eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-5900000000-cebbab9b4ecbc1be6c11View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink