Home Other Building Blocks Uridine 5'-(trihydrogen diphosphate), P'-α-D-galactopyranosyl ester, sodium salt (1:2)

Uridine 5'-(trihydrogen diphosphate), P'-α-D-galactopyranosyl ester, sodium salt (1:2)

CAS No.:
137868-52-1
Catalog Number:
AG0013ZN
Molecular Formula:
C15H22N2Na2O17P2
Molecular Weight:
610.2654
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
Product Description
Catalog Number:
AG0013ZN
Chemical Name:
Uridine 5'-(trihydrogen diphosphate), P'-α-D-galactopyranosyl ester, sodium salt (1:2)
CAS Number:
137868-52-1
Molecular Formula:
C15H22N2Na2O17P2
Molecular Weight:
610.2654
MDL Number:
MFCD00077895
IUPAC Name:
disodium;[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate
InChI:
InChI=1S/C15H24N2O17P2.2Na/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25;;/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25);;/q;2*+1/p-2/t5-,6-,8+,9-,10+,11-,12-,13-,14-;;/m1../s1
InChI Key:
PKJQEQVCYGYYMM-QKYKBPIOSA-L
SMILES:
OC[C@H]1O[C@H](OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2ccc(=O)[nH]c2=O)[O-])[O-])[C@@H]([C@H]([C@H]1O)O)O.[Na+].[Na+]
Properties
Complexity:
948  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
3  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
610.019g/mol
Formal Charge:
0
Heavy Atom Count:
38  
Hydrogen Bond Acceptor Count:
17  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0
Molecular Weight:
610.265g/mol
Monoisotopic Mass:
610.019g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
297A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal. Carbohydrate research 20121001
Gene regulation of UDP-galactose synthesis and transport: potential rate-limiting processes in initiation of milk production in humans. American journal of physiology. Endocrinology and metabolism 20120801
UDP-galactose 4'-epimerase activities toward UDP-Gal and UDP-GalNAc play different roles in the development of Drosophila melanogaster. PLoS genetics 20120501
Characterization of UDP-glucose 4-epimerase from Pyrococcus horikoshii: regeneration of UDP to produce UDP-galactose using two-enzyme system with trehalose. Bioresource technology 20120401
Structural insight into the unique substrate binding mechanism and flavin redox state of UDP-galactopyranose mutase from Aspergillus fumigatus. The Journal of biological chemistry 20120330
Efficient one-pot multienzyme synthesis of UDP-sugars using a promiscuous UDP-sugar pyrophosphorylase from Bifidobacterium longum (BLUSP). Chemical communications (Cambridge, England) 20120311
The C-terminal domain of the Salmonella enterica WbaP (UDP-galactose:Und-P galactose-1-phosphate transferase) is sufficient for catalytic activity and specificity for undecaprenyl monophosphate. Glycobiology 20120101
UDP-xylose and UDP-galactose synthesis in Trichomonas vaginalis. Molecular and biochemical parasitology 20120101
Overexpression of UDP-GlcNAc transporter partially corrects galactosylation defect caused by UDP-Gal transporter mutation. FEBS letters 20111003
Comparative analysis of involvement of UGT1 and UGT2 splice variants of UDP-galactose transporter in glycosylation of macromolecules in MDCK and CHO cell lines. Glycoconjugate journal 20111001
Enhanced UDP-glucose and UDP-galactose by homologous overexpression of UDP-glucose pyrophosphorylase in Lactobacillus casei. Journal of biotechnology 20110720
Newborn screening for galactosemia by a second-tier multiplex enzyme assay using UPLC-MS/MS in dried blood spots. Journal of inherited metabolic disease 20110401
The first C-glycosidic analogue of a novel galactosyltransferase inhibitor. Organic & biomolecular chemistry 20110321
Biosynthesis of UDP-xylose and UDP-arabinose in Sinorhizobium meliloti 1021: first characterization of a bacterial UDP-xylose synthase, and UDP-xylose 4-epimerase. Microbiology (Reading, England) 20110101
Promiscuous activity of ER glucosidase II discovered through donor specificity analysis of UGGT. Biochemical and biophysical research communications 20101217
Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches. Bioorganic & medicinal chemistry letters 20100815
A novel fluorescent probe for retaining galactosyltransferases. Chembiochem : a European journal of chemical biology 20100705
Direct non-radioactive assay of galactose-1-phosphate:uridyltransferase activity using high performance liquid chromatography. Clinica chimica acta; international journal of clinical chemistry 20100704
Enzymatic synthesis of Gb3 and iGb3 ceramides. Carbohydrate research 20100702
Characterization of rice nucleotide sugar transporters capable of transporting UDP-galactose and UDP-glucose. Journal of biochemistry 20100701
Deletion of UDP-glucose pyrophosphorylase reveals a UDP-glucose independent UDP-galactose salvage pathway in Leishmania major. Glycobiology 20100701
Binding of an acceptor substrate analog enhances the enzymatic activity of human blood group B galactosyltransferase. Glycobiology 20100601
Identification of essential amino acid residues in the hydrophilic loop regions of the CMP-sialic acid transporter and UDP-galactose transporter. Glycobiology 20100601
Characterization of two different types of UDP-glucose/-galactose 4-epimerase involved in galactosylation in fission yeast. Microbiology (Reading, England) 20100301
Quantification of extracellular UDP-galactose. Analytical biochemistry 20100101
UDP-sugar biosynthetic pathway: contribution to cyanidin 3-galactoside biosynthesis in apple skin. Planta 20091001
En route to deoxygenated N-acetyllactosamine analogues employing uridyl and galactosyl transferases. Carbohydrate research 20090817
Determination of beta4-galactosyltransferase-7 activity using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. Clinical biochemistry 20090401
UDP-glucose modulates gastric function through P2Y14 receptor-dependent and -independent mechanisms. American journal of physiology. Gastrointestinal and liver physiology 20090401
Potent ligands for prokaryotic UDP-galactopyranose mutase that exploit an enzyme subsite. Organic letters 20090101
Screening a limited structure-based library identifies UDP-GalNAc-specific mutants of alpha-1,3-galactosyltransferase. Glycobiology 20081201
UGE1 and UGE2 regulate the UDP-glucose/UDP-galactose equilibrium in Cryptococcus neoformans. Eukaryotic cell 20081201
Structural basis of UDP-galactose binding by alpha-1,3-galactosyltransferase (alpha3GT): role of negative charge on aspartic acid 316 in structure and activity. Biochemistry 20080819
Virulence attenuation of a UDP-galactose/N-acetylglucosamine beta1,4 galactosyltransferase expressing Leishmania donovani promastigote. Glycoconjugate journal 20080701
A single Caenorhabditis elegans Golgi apparatus-type transporter of UDP-glucose, UDP-galactose, UDP-N-acetylglucosamine, and UDP-N-acetylgalactosamine. Biochemistry 20080408
Synthesis and photolytic activation of 6''-O-2-nitrobenzyl uridine-5'-diphosphogalactose: a 'caged' UDP-Gal derivative. Carbohydrate research 20080407
Galactosylation does not prevent the rapid clearance of long-term, 4 degrees C-stored platelets. Blood 20080315
The involvement of beta-1,4-Galactosyltransferase and N-Acetylglucosamine residues in fertilization has been lost in the horse. Reproductive biology and endocrinology : RB&E 20080101
Synthesis of fluorescently labelled and internally quenched UDP-Gal probes. Carbohydrate research 20070903
Functional analysis of a lipid galactosyltransferase synthesizing the major envelope lipid in the Lyme disease spirochete Borrelia burgdorferi. FEMS microbiology letters 20070701
The mechanism of galactosamine toxicity revisited; a metabonomic study. Journal of proteome research 20070701
Site-directed mutagenesis of UDP-galactopyranose mutase reveals a critical role for the active-site, conserved arginine residues. Biochemistry 20070612
Two functionally divergent UDP-Gal nucleotide sugar transporters participate in phosphoglycan synthesis in Leishmania major. The Journal of biological chemistry 20070511
UDP-glucose 4-epimerase isoforms UGE2 and UGE4 cooperate in providing UDP-galactose for cell wall biosynthesis and growth of Arabidopsis thaliana. The Plant cell 20070501
[Experimental study on cryopreservation of platelets]. Zhongguo shi yan xue ye xue za zhi 20070401
[Cold storage of rabbit platelet suspension by adding uridine diphosphate galactose]. Zhongguo shi yan xue ye xue za zhi 20061201
Fragment-based screening of the donor substrate specificity of human blood group B galactosyltransferase using saturation transfer difference NMR. The Journal of biological chemistry 20061027
Blood group B galactosyltransferase: insights into substrate binding from NMR experiments. Journal of the American Chemical Society 20061018
Trypanosoma brucei UDP-galactose-4'-epimerase in ternary complex with NAD+ and the substrate analogue UDP-4-deoxy-4-fluoro-alpha-D-galactose. Acta crystallographica. Section F, Structural biology and crystallization communications 20060901
Immobilization of UDP-galactose 4-epimerase from Escherichia coli on the yeast cell surface. Bioscience, biotechnology, and biochemistry 20060901
Functional expression of the P2Y14 receptor in human neutrophils. European journal of pharmacology 20060814
Metabolism associated with raised metabolic flux to sugar nucleotide precursors of exopolysaccharides in Lactobacillus delbrueckii subsp. bulgaricus. Journal of industrial microbiology & biotechnology 20060501
Stereoselective synthesis of alpha-C-Substituted 1,4-dideoxy-1,4-imino-D-galactitols. Toward original UDP-Galf mimics via cross-metathesis. Organic letters 20060330
Modest phenotypic improvements in ASA-deficient mice with only one UDP-galactose:ceramide-galactosyltransferase gene. Lipids in health and disease 20060101
[Evaluation of the effects of glycosylation on in vivo survival of cold-storage human platelets by using rabbit model]. Zhongguo shi yan xue ye xue za zhi 20051201
AtUTr2 is an Arabidopsis thaliana nucleotide sugar transporter located in the Golgi apparatus capable of transporting UDP-galactose. Planta 20051001
Golgi and endoplasmic reticulum functions take place in different subcellular compartments of Entamoeba histolytica. The Journal of biological chemistry 20050916
Assaying uridine diphosphoglucose dehydrogenase in the presence of alcohol dehydrogenase. Analytical biochemistry 20050801
Identification and active expression of the Mycobacterium tuberculosis gene encoding 5-phospho-{alpha}-d-ribose-1-diphosphate: decaprenyl-phosphate 5-phosphoribosyltransferase, the first enzyme committed to decaprenylphosphoryl-d-arabinose synthesis. The Journal of biological chemistry 20050701
Amino-acid substitution in the disordered loop of blood group B-glycosyltransferase enzyme causes weak B phenotype. Transfusion 20050701
Synthesis and evaluation of mimetics of UDP and UDP-alpha-D-galactose, dTDP and dTDP-alpha-D-glucose with monosaccharides replacing the key pyrophosphate unit. Organic & biomolecular chemistry 20050321
Mutation of arginine 228 to lysine enhances the glucosyltransferase activity of bovine beta-1,4-galactosyltransferase I. Biochemistry 20050308
Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187. Bioorganic & medicinal chemistry letters 20050215
srf-3, a mutant of Caenorhabditis elegans, resistant to bacterial infection and to biofilm binding, is deficient in glycoconjugates. The Journal of biological chemistry 20041217
Primordial germ cell migration in the rat: preliminary evidence for a role of galactosyltransferase. Biology of reproduction 20041201
Effect of the Met344His mutation on the conformational dynamics of bovine beta-1,4-galactosyltransferase: crystal structure of the Met344His mutant in complex with chitobiose. Biochemistry 20041005
UDP-galactose 4-epimerase from Kluyveromyces fragilis: analysis of its hysteretic behavior during catalysis. Biochemistry 20040810
Refinement of the conformation of UDP-galactose bound to galactosyltransferase using the STD NMR intensity-restrained CORCEMA optimization. Journal of the American Chemical Society 20040721
Loss of srf-3-encoded nucleotide sugar transporter activity in Caenorhabditis elegans alters surface antigenicity and prevents bacterial adherence. The Journal of biological chemistry 20040716
Specificity of a soluble UDP-galactose: fucoside alpha1,3-galactosyltransferase that modifies the cytoplasmic glycoprotein Skp1 in Dictyostelium. The Journal of biological chemistry 20040709
Intermediate trapping on a mutant retaining alpha-galactosyltransferase identifies an unexpected aspartate residue. The Journal of biological chemistry 20040702
Identification of elongating beta-1,4-galactosyltransferase activity in mung bean (Vigna radiata) hypocotyls using 2-aminobenzaminated 1,4-linked beta- D-galactooligosaccharides as acceptor substrates. Planta 20040601
A unique catalytic mechanism for UDP-galactopyranose mutase. Nature structural & molecular biology 20040601
A new role for an old cofactor. Nature structural & molecular biology 20040601
Nucleotides in sow colostrum and milk at different stages of lactation. Journal of animal science 20040501
Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide. Carbohydrate research 20040428
Molecular dynamics simulations of glycosyltransferase LgtC. Carbohydrate research 20040402
Molecular modeling insights into the catalytic mechanism of the retaining galactosyltransferase LgtC. Carbohydrate research 20040402
Uridine 5'-polyphosphates (p4U and p5U) and uridine(5')polyphospho(5')nucleosides (Up(n)Ns) can be synthesized by UTP:glucose-1-phosphate uridylyltransferase from Saccharomyces cerevisiae. FEBS letters 20040312
Growth regulators and the control of nucleotide sugar flux. The Plant cell 20040301
A new strategy for the synthesis of glycoproteins. Science (New York, N.Y.) 20040116
Synthesis of uridine 5'-[2-S-pyridyl-3-thio-alpha-D-galactopyranosyl diphosphate]: precursor of UDP-thiogal sugar nucleotide donor substrate for beta-1,4-galactosyltransferase. Nucleosides, nucleotides & nucleic acids 20040101
Differential roles of the Leloir pathway enzymes and metabolites in defining galactose sensitivity in yeast. Molecular genetics and metabolism 20040101
A novel polygalacturonic acid bioflocculant REA-11 produced by Corynebacterium glutamicum: a proposed biosynthetic pathway and experimental confirmation. Applied microbiology and biotechnology 20031201
Roles of individual enzyme-substrate interactions by alpha-1,3-galactosyltransferase in catalysis and specificity. Biochemistry 20031125
Structure and function of enzymes of the Leloir pathway for galactose metabolism. The Journal of biological chemistry 20031107
Disruption of the two digalactosyldiacylglycerol synthase genes DGD1 and DGD2 in Arabidopsis reveals the existence of an additional enzyme of galactolipid synthesis. The Plant cell 20031101
Glycosylation restores survival of chilled blood platelets. Science (New York, N.Y.) 20030912
Refolding from denatured inclusion bodies, purification to homogeneity and simplified assay of MGDG synthases from land plants. Protein expression and purification 20030901
Comparison of the closed conformation of the beta 1,4-galactosyltransferase-1 (beta 4Gal-T1) in the presence and absence of alpha-lactalbumin (LA). Journal of biomolecular structure & dynamics 20030801
Expression of alpha-gal epitopes on ovarian carcinoma membranes to be used as a novel autologous tumor vaccine. Gynecologic oncology 20030701
Substrate recognition by nucleotide sugar transporters: further characterization of substrate recognition regions by analyses of UDP-galactose/CMP-sialic acid transporter chimeras and biochemical analysis of the substrate specificity of parental and chimeric transporters. The Journal of biological chemistry 20030620
Proteoglycan UDP-galactose:beta-xylose beta 1,4-galactosyltransferase I is essential for viability in Drosophila melanogaster. The Journal of biological chemistry 20030502
Interdependence of backbone flexibility, residue conservation, and enzyme function: a case study on beta1,4-galactosyltransferase-I. Biochemistry 20030408
Potentiometric analysis of UDP-galactopyranose mutase: stabilization of the flavosemiquinone by substrate. Biochemistry 20030225
A method for the generation of glycoprotein mimetics. Journal of the American Chemical Society 20030219
Metabolism of 13C galactose by lymphoblasts from patients with galactosemia determined by NMR spectroscopy. Molecular genetics and metabolism 20021201
Thiosugar nucleotide analogs: synthesis of 5'-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-alpha-D-galactopyranosyl diphosphate). Carbohydrate research 20021119
Muscle uridine diphosphate-hexosamines do not decrease despite correction of hyperglycemia-induced insulin resistance in type 2 diabetes. The Journal of clinical endocrinology and metabolism 20021101
Galactose biosynthesis in Arabidopsis: genetic evidence for substrate channeling from UDP-D-galactose into cell wall polymers. Current biology : CB 20021029
Transport of UDP-galactose in plants. Identification and functional characterization of AtUTr1, an Arabidopsis thaliana UDP-galactos/UDP-glucose transporter. The Journal of biological chemistry 20020906
Transfer specificity of detergent-solubilized fenugreek galactomannan galactosyltransferase. Plant physiology 20020701
Crystal structure of beta1,4-galactosyltransferase complex with UDP-Gal reveals an oligosaccharide acceptor binding site. Journal of molecular biology 20020426
Mechanistic studies of a retaining alpha-galactosyltransferase from Neisseria meningitidis. Biochemistry 20020423
Combined biosynthetic pathway for de novo production of UDP-galactose: catalysis with multiple enzymes immobilized on agarose beads. Chembiochem : a European journal of chemical biology 20020402
Deficiency of UDP-galactose:N-acetylglucosamine beta-1,4-galactosyltransferase I causes the congenital disorder of glycosylation type IId. The Journal of clinical investigation 20020315
DGD2, an arabidopsis gene encoding a UDP-galactose-dependent digalactosyldiacylglycerol synthase is expressed during growth under phosphate-limiting conditions. The Journal of biological chemistry 20020111
Human and Drosophila UDP-galactose transporters transport UDP-N-acetylgalactosamine in addition to UDP-galactose. European journal of biochemistry 20020101
Functional assignment of motifs conserved in beta 1,3-glycosyltransferases. European journal of biochemistry 20020101
Chemoenzymatic synthesis of biotinylated nucleotide sugars as substrates for glycosyltransferases. Chembiochem : a European journal of chemical biology 20011203
Thiosugar nucleotide analogues: synthesis of uridine 5'-(2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-alpha-D-galactopyranosyl diphosphate). Carbohydrate research 20011008
Structure of bovine alpha-1,3-galactosyltransferase and its complexes with UDP and DPGal inferred from molecular modeling. Proteins 20010901
The Saccharomyces cerevisiae MLF6/YPL244C gene, which encodes a possible yeast homologue of mammalian UDP-galactose transporter, confers resistance to the immunosuppressive drug, leflunomide. Current microbiology 20010801
Glycoengineering of therapeutic glycoproteins: in vitro galactosylation and sialylation of glycoproteins with terminal N-acetylglucosamine and galactose residues. Biochemistry 20010731
Characterization of a Schizosaccharomyces pombe mutant deficient in UDP-galactose transport activity. Yeast (Chichester, England) 20010701
Solubilization of rhamnogalacturonan I galactosyltransfrases from membranes of a flax cell suspension. Planta 20010701
Crystal structure of lactose synthase reveals a large conformational change in its catalytic component, the beta1,4-galactosyltransferase-I. Journal of molecular biology 20010629
Substrate recognition by UDP-galactose and CMP-sialic acid transporters. Different sets of transmembrane helices are utilized for the specific recognition of UDP-galactose and CMP-sialic acid. The Journal of biological chemistry 20010615
Human UDP-galactose 4-epimerase. Accommodation of UDP-N-acetylglucosamine within the active site. The Journal of biological chemistry 20010504
Galactose metabolism in normal human lymphoblasts studied by (1)H, (13)C and (31)P NMR spectroscopy of extracts. NMR in biomedicine 20010501
Bovine alpha1,3-galactosyltransferase catalytic domain structure and its relationship with ABO histo-blood group and glycosphingolipid glycosyltransferases. The EMBO journal 20010215
Crystal structure of the retaining galactosyltransferase LgtC from Neisseria meningitidis in complex with donor and acceptor sugar analogs. Nature structural biology 20010201
Chemical synthesis of UDP-beta-L-arabinofuranose and its turnover to UDP-beta-L-arabinopyranose by UDP-galactopyranose mutase. Bioorganic & medicinal chemistry letters 20010122
An HPLC method for the assay of UDP-glucose pyrophosphorylase and UDP-glucose-4-epimerase in Solieria chordalis (Rhodophyceae). Phytochemical analysis : PCA 20010101
Simultaneous, quantitative analysis of UDP-N-acetylglucosamine, UDP-N-acetylgalactosamine, UDP-glucose and UDP-galactose in human peripheral blood cells, muscle biopsies and cultured mesangial cells by capillary zone electrophoresis. Electrophoresis 20000801
Molecular cloning and characterization of a novel isoform of the human UDP-galactose transporter, and of related complementary DNAs belonging to the nucleotide-sugar transporter gene family. Journal of biochemistry 19961201
Human UDP-galactose translocator: molecular cloning of a complementary DNA that complements the genetic defect of a mutant cell line deficient in UDP-galactose translocator. Journal of biochemistry 19960801
RNA polymerase II is a glycoprotein. Modification of the COOH-terminal domain by O-GlcNAc. The Journal of biological chemistry 19930515
Properties