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D-Ribitol-5-phosphate

CAS# 35320-17-3

D-Ribitol-5-phosphate

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Chemical structure

D-Ribitol-5-phosphate

3D structure

Chemical Properties of D-Ribitol-5-phosphate

Cas No. 35320-17-3 SDF Download SDF
PubChem ID 151104 Appearance Powder
Formula C5H13O8P M.Wt 232.12
Type of Compound N/A Storage Desiccate at -20°C
Synonyms D-Ribitol 5-phosphate;Ribitol-5-phosphate;Ribitol 5-phosphate
Solubility Soluble in DMSO > 10 mM
Chemical Name [(2R,3S,4S)-2,3,4,5-tetrahydroxypentyl] dihydrogen phosphate
SMILES C(C(C(C(COP(=O)(O)O)O)O)O)O
Standard InChIKey VJDOAZKNBQCAGE-LMVFSUKVSA-N
Standard InChI InChI=1S/C5H13O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h3-9H,1-2H2,(H2,10,11,12)/t3-,4+,5-/m0/s1
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.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of D-Ribitol-5-phosphate

DescriptionRibitol is a crystalline pentose alcohol formed by the reduction of ribose. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol.In Vitro:Ribitol is a reduced sugar[1]. Phosphoglucose isomerase-deficient (pgi1) strains of Saccharomyces cerevisiae are studied for the production of D-ribose and Ribitol from D-glucose via the intermediates of the pentose phosphate pathway. Overexpression of the gene encoding sugar phosphate phosphatase (DOG1) of S. cerevisiae is needed for the production of D-ribose and Ribitol. The engineered strains are compared for their ability to produce the PPP-derived 5-carbon compounds Ribitol and D-ribose from D-glucose[2].

References:
[1]. Praissman JL, et al. The functional O-mannose glycan on α-dystroglycan contains a phospho-Ribitol primed for matriglycan addition. Elife. 2016 Apr 29;5. pii: e14473. [2]. Toivari MH, et al. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol. Appl Microbiol Biotechnol. 2010 Jan;85(3):731-9.

Protocol

Kinase Assay [2]
The high-performance liquid chromatography (HPLC) analyses are carried out using a Fast Acid Column (100×7.8 mm) and a HPX-87H Ion Exclusion Column (300 mm×7.8 mm) in series with 2.5 mM H2SO4 in water as the mobile phase at a flow rate of 0.3 mL/min, at 55°C. This method enabled quantification of D-glucose, ethanol, glycerol, D-xylulose, Ribitol, and xylitol. D-ribose, D-ribulose, and D-arabitol coeluted on the Aminex HPX-87H column. The CarboPac MA-1 column of Dionex ICS-3000 is used to analyze representative culture supernatant samples for the presence of arabitol and xylitol. Samples are run at column temperature of 30°C with 480 mM NaOH at flow rate 0.4 mL/min. The CarboPac MA-1 column separated D-arabitol from D-ribose and D-ribulose, but the alkaline conditions degraded D-ribulose interfering with the quantification of D-ribose.Yeast cells are disrupted with glass beads in 100 mM sodium phosphate buffer pH 7.0 containing phenylmethylsulfonyl fluoride and pepstatin A in final concentrations of 0.17 mg/mL and 0.01 mg/mL, respectively.The activity of NAD+-dependent Gdh2p is measured in a reaction buffer of 0.5 M triethanol amine pH 7.7 and 2 mM NADH. After addition of the cell lysate, the reaction is started by adding a mixture of α-ketoglutarate (100 mM) and NH4Cl (200 mM) to a final concentration of 2.4 mM and 4.9 mM, respectively. The GapB activity is measured. Shortly, the reaction mixture is 500 mM triethanol amine pH 7.8, 1 mM ATP, 2 mM MgCl2, 200 μM NADPH, and 10 μg/mL of phosphoglycerate kinase. 3-phosphoglycerate is added to a final concentration of 5 mM to start the reaction. Activity measurements are performed with a Cobas Mira Plus automated analyzer[2].

References:
[1]. Praissman JL, et al. The functional O-mannose glycan on α-dystroglycan contains a phospho-Ribitol primed for matriglycan addition. Elife. 2016 Apr 29;5. pii: e14473. [2]. Toivari MH, et al. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol. Appl Microbiol Biotechnol. 2010 Jan;85(3):731-9.

D-Ribitol-5-phosphate Dilution Calculator

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D-Ribitol-5-phosphate Molarity Calculator

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Preparing Stock Solutions of D-Ribitol-5-phosphate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.3081 mL 21.5406 mL 43.0812 mL 86.1623 mL 107.7029 mL
5 mM 0.8616 mL 4.3081 mL 8.6162 mL 17.2325 mL 21.5406 mL
10 mM 0.4308 mL 2.1541 mL 4.3081 mL 8.6162 mL 10.7703 mL
50 mM 0.0862 mL 0.4308 mL 0.8616 mL 1.7232 mL 2.1541 mL
100 mM 0.0431 mL 0.2154 mL 0.4308 mL 0.8616 mL 1.077 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on D-Ribitol-5-phosphate

Ribitol is a crystalline pentose alcohol and is formed by the reduction of ribose which is occurs naturally in the plant Adonis vernalis.

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References on D-Ribitol-5-phosphate

ISPD produces CDP-ribitol used by FKTN and FKRP to transfer ribitol phosphate onto alpha-dystroglycan.[Pubmed:27194101]

Nat Commun. 2016 May 19;7:11534.

Mutations in genes required for the glycosylation of alpha-dystroglycan lead to muscle and brain diseases known as dystroglycanopathies. However, the precise structure and biogenesis of the assembled glycan are not completely understood. Here we report that three enzymes mutated in dystroglycanopathies can collaborate to attach ribitol phosphate onto alpha-dystroglycan. Specifically, we demonstrate that isoprenoid synthase domain-containing protein (ISPD) synthesizes CDP-ribitol, present in muscle, and that both recombinant fukutin (FKTN) and fukutin-related protein (FKRP) can transfer a ribitol phosphate group from CDP-ribitol to alpha-dystroglycan. We also show that ISPD and FKTN are essential for the incorporation of ribitol into alpha-dystroglycan in HEK293 cells. Glycosylation of alpha-dystroglycan in fibroblasts from patients with hypomorphic ISPD mutations is reduced. We observe that in some cases glycosylation can be partially restored by addition of ribitol to the culture medium, suggesting that dietary supplementation with ribitol should be evaluated as a therapy for patients with ISPD mutations.

The Muscular Dystrophy Gene TMEM5 Encodes a Ribitol beta1,4-Xylosyltransferase Required for the Functional Glycosylation of Dystroglycan.[Pubmed:27733679]

J Biol Chem. 2016 Nov 18;291(47):24618-24627.

A defect in O-mannosyl glycan is the cause of alpha-dystroglycanopathy, a group of congenital muscular dystrophies caused by aberrant alpha-dystroglycan (alpha-DG) glycosylation. Recently, the entire structure of O-mannosyl glycan, [3GlcAbeta1-3Xylalpha1]n-3GlcAbeta1-4Xyl-Rbo5P-1Rbo5P-3GalNAcbeta1-3GlcNAcbeta1-4 (phospho-6)Manalpha1-, which is required for the binding of alpha-DG to extracellular matrix ligands, has been proposed. However, the linkage of the first Xyl residue to ribitol 5-phosphate (Rbo5P) is not clear. TMEM5 is a gene product responsible for alpha-dystroglycanopathy and was reported as a potential enzyme involved in this linkage formation, although the experimental evidence is still incomplete. Here, we report that TMEM5 is a xylosyltransferase that forms the Xylbeta1-4Rbo5P linkage on O-mannosyl glycan. The anomeric configuration and linkage position of the product (beta1,4 linkage) was determined by NMR analysis. The introduction of two missense mutations in TMEM5 found in alpha-dystroglycanopathy patients impaired xylosyltransferase activity. Furthermore, the disruption of the TMEM5 gene by CRISPR/Cas9 abrogated the elongation of the (-3GlcAbeta1-3Xylalpha1-) unit on O-mannosyl glycan. Based on these results, we concluded that TMEM5 acts as a UDP-d-xylose:ribitol-5-phosphate beta1,4-xylosyltransferase in the biosynthetic pathway of O-mannosyl glycan.

The functional O-mannose glycan on alpha-dystroglycan contains a phospho-ribitol primed for matriglycan addition.[Pubmed:27130732]

Elife. 2016 Apr 29;5.

Multiple glycosyltransferases are essential for the proper modification of alpha-dystroglycan, as mutations in the encoding genes cause congenital/limb-girdle muscular dystrophies. Here we elucidate further the structure of an O-mannose-initiated glycan on alpha-dystroglycan that is required to generate its extracellular matrix-binding polysaccharide. This functional glycan contains a novel ribitol structure that links a phosphotrisaccharide to xylose. ISPD is a CDP-ribitol (ribose) pyrophosphorylase that generates the reduced sugar nucleotide for the insertion of ribitol in a phosphodiester linkage to the glycoprotein. TMEM5 is a UDP-xylosyl transferase that elaborates the structure. We demonstrate in a zebrafish model as well as in a human patient that defects in TMEM5 result in muscular dystrophy in combination with abnormal brain development. Thus, we propose a novel structure-a ribitol in a phosphodiester linkage-for the moiety on which TMEM5, B4GAT1, and LARGE act to generate the functional receptor for ECM proteins having LG domains.

Immunoassays for riboflavin and flavin mononucleotide using antibodies specific to d-ribitol and d-ribitol-5-phosphate.[Pubmed:28327345]

J Immunol Methods. 2017 Jun;445:59-66.

Riboflavin (vitamin B2), a water-soluble vitamin, plays a key role in maintaining human health. Though, numerous methods have been reported for the determination of total riboflavin (TRF) content in foods and biological samples, very few methods are reported for quantifying riboflavin and its coenzymes [flavin mononucleotide (FMN); flavin adenine dinucleotide (FAD)] individually. Recently, we have demonstrated that antibodies specific to d-ribitol and D-Ribitol-5-phosphate also recognize riboflavin and FMN, respectively, and not vice-versa. In this study, we have evaluated these two antibodies for the analysis of riboflavin and FMN by indirect competitive ELISA (icELISA) in selected foods and pharmaceuticals. Under the optimal assay conditions, 50% inhibition concentration (IC50) and limit of detection (LOD, IC10) were 3.41ng/mL and 0.02ng/mL for riboflavin, and 7.84ng/mL and 0.24ng/mL for FMN, respectively, with detectable concentration range between 0.1 and 100ng of analytes and <0.1% cross-reactivity with other water-soluble vitamins. The amounts of TRF in food samples, as analyzed by icELISA using ribitol antibody, were 90-95% of the reported values in the literature or label values. Quantification of individual flavins (riboflavin and FMN) from the same food samples showed variation in their values compared to TRF, and were in good agreement with values obtained from HPLC and AOAC methods. Further, spiking and recovery analysis of food samples and pharmaceuticals showed no significant matrix effects. The immunoassays were validated in terms of accuracy and precision using inter- and intra-assays. The immunoassays developed in this study are sensitive and appears feasible for screening a large number of samples in the quantification of riboflavin and FMN in various biological samples, pharmaceuticals and natural/processed foods.

Description

Ribitol is a crystalline pentose alcohol and is formed by the reduction of ribose which is occurs naturally in the plant Adonis vernalis.

Keywords:

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