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Uridine diphosphate glucose

Catalog No.GC37866

Uridine diphosphate glucose Chemical Structure

Uridine diphosphate glucose (uracil-diphosphate glucose, UDPG) is a nucleotide sugar.

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Sample solution is provided at 25 µL, 10mM.

Quality Control

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Protocol

Cell experiment [1]:

Cell lines

S. cerevisiae alg6 cells (PRY103) transformed with plasmids p426GPD or p426GPD-gpt1+

Preparation Method

The C-terminal end of S. pombe GT was mutated from PDEL to the S. cerevisiae retrieval signal HDEL, and the GT-encoding gene, gpt1+, was then inserted in high-copy number expression vectors (p426GPD) under the glyceraldehyde 3-P dehydrogenase promoter. S. cerevisiae alg6 cells (PRY103) were then transformed with the expression vectors with or without S. pombe gpt1+ gene.

Reaction Conditions

S. cerevisiae alg6 mutant (PRY103) cells transformed with p426GPD-gpt1+ or with p426GPD were incubated with [14C]glucose for 15 min in the presence or absence of DNJ. N-linked oliogosaccharides were regarded as the indication.

Applications

Uridine diphosphate glucose could be transported into the ER of Saccharomyces cerevisiae in vivo and into ER–containing microsomes in vitro. Uridine diphosphate glucose helps with the synthesis of b-1,6-glucan, one of Saccharomyces cerevisiae cell wall components, in the lumen of the endoplasmic reticulum (ER).

Animal experiment [2]:

Animal models

Balb/c mice; CRF1 mice; CD8 mice

Preparation Method

Mice of various strains, Balb/c, CD8, and CRF 1with and without tumor implants, maintained on Purina rat chow and tap water, were infused intraperitoneally with a phosphate-buffered saline (PBS) solution of Uridine diphosphate glucose at a constant rate of 0.8 ml/day for 5 days.

Dosage form

8 and 80 mM (0.28 and2.8 mmoles/kg body weight/day)

Applications

Uridine diphosphate glucose (UDPG) is shown to have tissue-specific effects that have proved to be of clinical value in the treatment of some liver ailments. The effects of Uridine diphosphate glucose on the levels of 5-phosphoribosyl pyrophosphate (PRPP) and PRPP synthetase in mouse liver, spleen and transplanted tumors are investigated to determine the mechanism of action with three stains of mice models.

References:

[1]. Olga C. et al. Uridine Diphosphate–Glucose Transport into the Endoplasmic Reticulum of Saccharomyces cerevisiae: In Vivo and In Vitro Evidence. Molecular Biology of the Cell 1999 Apr; 10, 1019–1030.

[2]. Yip LC, et al. Effects of uridine diphosphoglucose (UDPG) infusion on 5-phosphoribosyl pyrophosphate (PRPP) levels of mouse tissues. Biochem Pharmacol. 1987 Mar 1;36(5):633-7.

Background

Uridine diphosphate glucose (uracil-diphosphate glucose, UDPG) is a nucleotide sugar. It is used in nucleotide sugar metabolism as an activated form of glucose, a substrate for enzymes called glucosyltransferases. [1] Uridine diphosphate glucose has been shown to have tissue-specific effects that have proved to be of clinical value in the treatment of some liver ailments. It is also known to have multiple effects on intrahepatic bilirubin metabolism which, in turn, are related to the glycogen synthesis occurring in the liver.[2]

In vitro study demonstrated that the effects of UDPG on cell metabolism do not appear to be limited to enzyme induction. Others have reported that UDPG can have effects under conditions that bar enzyme induction. Results showed that a significant amount of the UDPG, even though it is a highly polar compound, does pass through the membrane unchanged. A large fraction of the UDPG added to incubation media, however, was found in the cell as glucose phosphate, indicating cleavage after penetration of the cell. Eventually. all the UDPG that entered the cells was degraded to glucose phosphate and glucose. The in vitro studies show that G-6-P is not the active form, and several tests show that uridine does not lead to changes like those seen with UDPG. [2]

In vivo study indicated that indicate that the intracellular level of PRPP in animal tissues is greatly affected by extracellular UDPG. The alteration of PRPP level by UDPG is not linearly dose-related. The changes in PRPP that were induced by UDPG were also tissue-specific: mouse liver was more sensitive than was the spleen. This latter specificity may well be related to the therapeutically beneficial effects of UDPG.[2]

References:
[1]. Rademacher T, Pet al. "Glycobiology". Annu Rev Biochem. 1988; 57: 785–838.
[2]. Yip LC, et al. Effects of uridine diphosphoglucose (UDPG) infusion on 5-phosphoribosyl pyrophosphate (PRPP) levels of mouse tissues. Biochem Pharmacol. 1987 Mar 1;36(5):633-7.

Chemical Properties

Cas No. 133-89-1 SDF
Synonyms N/A
Chemical Name N/A
Canonical SMILES OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OP(OP(OC[C@@H]2O[C@@H](N3C=CC(NC3=O)=O)[C@H](O)[C@@H]2O)(O)=O)(O)=O)O)O)O
Formula C15H24N2O17P2 M.Wt 566.3
Solubility H2O : ≥ 50 mg/mL Storage Store at -20°C, protect from light, stored under nitrogen
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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Research Update

Studies on uridine diphosphate glucose

Biochem J1952 Jun;51(3):426-30.PMID: 12977745DOI: 10.1042/bj0510426

The recent disproof of a major deficiency of uridine diphosphate galactose in galactosemia should not lead investigators to assume either that enzymatic methods are unreliable for uridine sugar assays or that a defect in galactosylation in galactosemia has been excluded.

Measurements of uridine diphosphate glucose and uridine diphosphate galactose--an appraisal

Eur J Pediatr1995;154(7 Suppl 2):S72-4.PMID: 7671969DOI: 10.1007/BF02143807

The recent disproof of a major deficiency of uridine diphosphate galactose in galactosemia should not lead investigators to assume either that enzymatic methods are unreliable for uridine sugar assays or that a defect in galactosylation in galactosemia has been excluded.

31 P-MRS of the healthy human brain at 7 T detects multiple hexose derivatives of uridine diphosphate glucose

NMR Biomed2021 Jul;34(7):e4511.PMID: 33772915DOI: 10.1002/nbm.4511

Nucleotide sugars are required for the synthesis of glycoproteins and glycolipids, which play crucial roles in many cellular functions such as cell communication and immune responses. uridine diphosphate glucose (UDP-Glc) was previously believed to be the only nucleotide sugar detectable in brain by 31 P-MRS. Using spectra of high SNR and high resolution acquired at 7 T, we showed that multiple nucleotide sugars are coexistent in brain and can be measured simultaneously. In addition to UDP-Glc, these also include UDP-galactose (UDP-Gal), -N-acetyl-glucosamine (UDP-GlcNAc) and -N-acetyl-galactosamine (UDP-GalNAc), collectively denoted as UDP(G). Coexistence of these UDP(G) species is evident from a quartet-like multiplet at -9.8 ppm (M-9.8 ), which is a common feature seen across a wide age range (24-64 years). Lineshape fitting of M-9.8 allows an evaluation of all four UDP(G) components, which further aids in analysis of a mixed signal at -8.2 ppm (M-8.2 ) for deconvolution of NAD+ and NADH. For a group of seven young healthy volunteers, the concentrations of UDP(G) species were 0.04 ± 0.01 mM for UDP-Gal, 0.07 ± 0.03 mM for UDP-Glc, 0.06 ± 0.02 mM for UDP-GalNAc and 0.08 ± 0.03 mM for UDP-GlcNA, in reference to ATP (2.8 mM). The combined concentration of all UDP(G) species (average 0.26 ± 0.06 mM) was similar to the pooled concentration of NAD+ and NADH (average 0.27 ± 0.06 mM, with a NAD+ /NADH ratio of 6.7 ± 2.1), but slightly lower than previously found in an older cohort (0.31 mM). The in vivo NMR analysis of UDP-sugar composition is consistent with those from tissue extracts by other modalities in the literature. Given that glycosylation is dependent on the availability of nucleotide sugars, assaying multiple nucleotide sugars may provide valuable insights into potential aberrant glycosylation, which has been implicated in certain diseases such as cancer and Alzheimer's disease.

uridine diphosphate glucose-BETA-1,3-GLUCAN BETA-3-GLUCOSYLTRANSFERASE FROM EUGLENA GRACILIS

J Biol Chem1964 Oct;239:3163-7.PMID: 14245356DOI: 10.1021/bi981884q

Toxoplasma gondii is an obligate intracellular parasite of the phylum apicomplexa and a common and often life-threatening opportunistic infection associated with AIDS. A family of parasite-specific glycosylphosphatidylinositols containing a novel glucosylated side chain has been shown to be highly immunogenic in humans (Striepen et al. (1997) J. Mol. Biol. 266, 797-813). In contrast to trypanosomes in T. gondii side chain modification takes place before addition to protein in the endoplasmic reticulum. The biosynthesis of these modifications was studied in an in vitro system prepared from hypotonically lysed T. gondii parasites. Radiolabeled glucose-containing glycosylphosphatidylinositol precursors were synthesized by T. gondii membrane preparations upon incubation with uridine diphosphate-[3H]glucose. Synthesis of glucosylated glycolipids took place only in the presence of exogenous uridine diphosphate glucose and was stimulated by unlabeled uridine diphosphate glucose in a dose-dependent manner. In contrast to glycosylphosphatidylinositol mannosylation, glucosylation was shown to be insensitive to amphomycin treatment. In addition, the glucose analogue 2-deoxy-D-glucose was used to trace the glycosylphosphatidylinositol glucosylation pathway. Detailed analysis of glycolipids synthesized in vitro in the presence of UDP and GDP derivatives of D-glucose and 2-deoxy-D-glucose ruled out an involvement of dolichol phosphate-glucose and demonstrates direct transfer of glucose from uridine diphosphate glucose.

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