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D-Sedoheptulose-7-phosphate barium

Alias: D-Sedoheptulose-7-phosphate barium salt
Cat No.:V89774 Purity: ≥98%
D-Sedoheptulose-7-phosphate barium is a common precursor of heptapeptides such as septacidin and hygromycin B.
D-Sedoheptulose-7-phosphate barium
D-Sedoheptulose-7-phosphate barium Chemical Structure CAS No.: 17187-72-3
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
D-Sedoheptulose-7-phosphate barium is a common precursor of heptapeptides such as septacidin and hygromycin B. D-Sedoheptulose-7-phosphate barium is converted to NDP-heptoses through a similar biosynthetic pathway.
D-Sedoheptulose-7-phosphate barium salt (CAS 17187-72-3) is an intermediate of the pentose phosphate pathway (PPP), a major glucose catabolic pathway generating NADPH and ribose-5-phosphate. It is a seven-carbon sugar phosphate with molecular formula C₇H13O10P·Ba and molecular weight 425.47. The barium salt form stabilizes the compound for isolation and storage. It is a biochemical reagent for studying carbohydrate metabolism and antibiotic biosynthesis.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
D-Sedoheptulose-7-phosphate functions as a substrate for the enzyme transaldolase in the non-oxidative phase of the pentose phosphate pathway. Transaldolase catalyzes the reversible transfer of a three-carbon dihydroxyacetone moiety from sedoheptulose-7-phosphate to glyceraldehyde-3-phosphate, generating erythrose-4-phosphate and fructose-6-phosphate. This reaction links the PPP to glycolysis and is essential for carbon rearrangement, nucleotide synthesis, and production of aromatic amino acid precursors.
ln Vitro
D-Sedoheptulose-7-phosphate is an intermediate in the pentose phosphate pathway, where transaldolase catalyzes the transfer of a three-carbon dihydroxyacetone moiety from sedoheptulose-7-phosphate to glyceraldehyde-3-phosphate to generate D-fructose-6-phosphate. It is also a common precursor for the biosynthesis of heptapeptides such as septacidin and hygromycin B, and is converted to NDP-heptoses through similar biosynthetic pathways. In cell-free assays, it serves as a substrate for transaldolase to study enzyme kinetics and PPP flux.
ln Vivo
D-Sedoheptulose-7-phosphate is not administered to animals as a drug, but as a metabolic intermediate it is used in ex vivo studies of pentose phosphate pathway activity. Tissue homogenates (e.g., liver or brain) can be supplemented with sedoheptulose-7-phosphate (0.1-1 mM) to measure transaldolase activity. In animal models of metabolic disorders, changes in sedoheptulose-7-phosphate levels can serve as a biomarker for PPP dysregulation. It is primarily a research tool, not a therapeutic.
Enzyme Assay
Transaldolase activity can be measured using a coupled enzyme assay. Reaction mixture (1 mL) contains 50 mM triethanolamine buffer (pH 7.4), 5 mM sedoheptulose-7-phosphate, 2 mM glyceraldehyde-3-phosphate, 0.2 mM NADH, and 5 units of glyceraldehyde-3-phosphate dehydrogenase/triose phosphate isomerase. The reaction is initiated by adding 10-50 ug of tissue homogenate or purified transaldolase. The decrease in absorbance at 340 nm is monitored for 10 min, and activity is calculated using an extinction coefficient of 6.22 mM-¹cm-¹.
Cell Assay
A cell-free system using purified transaldolase is employed for kinetic studies. Transaldolase (0.1-1.0 ug) is incubated with varying concentrations of D-Sedoheptulose-7-phosphate (0.01-5 mM) and a fixed concentration of glyceraldehyde-3-phosphate (2 mM) in 50 mM triethanolamine buffer (pH 7.4) at 25degC for 10 min. The product erythrose-4-phosphate is quantified by HPLC with UV detection or by coupled enzyme assay. Kinetic parameters (Km, Vmax) are calculated from Michaelis-Menten plots. Transaldolase exhibits a Km of approximately 0.5-1 mM for sedoheptulose-7-phosphate.
Animal Protocol
For cellular studies, cells (e.g., hepatocytes or cancer cell lines) are cultured in glucose-containing medium. D-Sedoheptulose-7-phosphate is not cell-permeable due to its phosphate group and barium content, so it is used in lysates or permeabilized cells. Cell lysates are prepared by sonication in PBS, and transaldolase activity is measured by adding sedoheptulose-7-phosphate (2 mM) to the lysate and quantifying fructose-6-phosphate production by HPLC or enzymatic assays. The contribution of the pentose phosphate pathway to cellular metabolism is assessed by measuring sedoheptulose-7-phosphate levels by LC-MS/MS.
ADME/Pharmacokinetics
D-Sedoheptulose-7-phosphate barium salt is not directly administered to animals due to the barium content, which is toxic. The compound is used ex vivo: tissue samples (e.g., liver, kidney, brain) are homogenized in buffer and centrifuged. The supernatant is incubated with 2 mM D-Sedoheptulose-7-phosphate for 30-60 min at 37degC. Transaldolase activity is measured by the production of fructose-6-phosphate or consumption of glyceraldehyde-3-phosphate. Changes in activity are correlated with metabolic disease states or drug treatments affecting the pentose phosphate pathway.
Toxicity/Toxicokinetics
The phosphate group makes D-Sedoheptulose-7-phosphate highly polar and water-soluble, but the compound does not readily cross cell membranes. The barium counterion is used for stabilization and precipitation during isolation but can be toxic; barium should be removed before biological assays by treatment with sodium sulfate to precipitate barium sulfate, leaving the free sugar phosphate in solution. The free acid form is preferred for enzymatic assays. For storage, the barium salt is stable at -20degC for up to 2 years. D-Sedoheptulose-7-phosphate is unstable at neutral to alkaline pH; solutions should be stored at pH 4-6.
References

[1]. d-Sedoheptulose-7-phosphate is a common precursor for the heptoses of septacidin and hygromycin B.Proc Natl Acad Sci U S A. 2018 Mar 13;115(11):2818-2823.

Additional Infomation
The barium salt form requires special handling due to barium toxicity. Barium compounds are toxic if ingested or inhaled, and can cause gastrointestinal disturbance, hypokalemia, and cardiac arrhythmias. The oral LD₅0 of barium salts in rats is approximately 200-500 mg/kg. The compound should be handled with extreme caution: avoid dust generation, use in a fume hood, wear appropriate PPE (gloves, goggles, lab coat). Spills should be cleaned with sodium sulfate to precipitate barium before disposal. It is not for human use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H15BAO10P
Molecular Weight
427.49
Exact Mass
425.929
CAS #
17187-72-3
PubChem CID
132285237
Appearance
Typically exists as solid at room temperature
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
3
Heavy Atom Count
19
Complexity
319
Defined Atom Stereocenter Count
5
SMILES
C([C@@H]1[C@H]([C@H]([C@@H]([C@](O1)(CO)O)O)O)O)OP(=O)([O-])[O-].[Ba+2]
InChi Key
CXUFELXUIHDDQP-CQJQEINESA-L
InChi Code
InChI=1S/C7H15O10P.Ba/c8-2-7(12)6(11)5(10)4(9)3(17-7)1-16-18(13,14)15;/h3-6,8-12H,1-2H2,(H2,13,14,15);/q;+2/p-2/t3-,4-,5-,6+,7-;/m1./s1
Chemical Name
barium(2+);[(2R,3S,4R,5S,6R)-3,4,5,6-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]methyl phosphate
Synonyms
D-Sedoheptulose-7-phosphate barium salt
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3392 mL 11.6962 mL 23.3924 mL
5 mM 0.4678 mL 2.3392 mL 4.6785 mL
10 mM 0.2339 mL 1.1696 mL 2.3392 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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