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2-O-DMT-Sulfonyldiethanol phosphoramidite (phosphorylated monomer)

Alias: 2-O-DMT-Sulfonyldiethanol phosphoramidite
Cat No.:V55123 Purity: ≥97%
2-O-DMT-Sulfonyldiethanol phosphoramidite is a phosphoramidite monomer that may be utilized in the solid-phase synthesis of oligonucleotides.
2-O-DMT-Sulfonyldiethanol phosphoramidite (phosphorylated monomer)
2-O-DMT-Sulfonyldiethanol phosphoramidite (phosphorylated monomer) Chemical Structure CAS No.: 108783-02-4
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
Other Sizes
Official Supplier of:
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Product Description
2-O-DMT-Sulfonyldiethanol phosphoramidite is a phosphoramidite monomer that may be utilized in the solid-phase synthesis of oligonucleotides.
2-O-DMT-Sulfonyldiethanol phosphoramidite (CAS 108783-02-4) is a specialized phosphoramidite monomer featuring a sulfonyldiethanol linker protected by a dimethoxytrityl (DMT) group at the 2'-O position. This compound serves as a phosphorylated monomer for introducing phosphate modifications or linker arms into synthetic oligonucleotides during solid-phase synthesis. Its molecular formula is C34H45N2O7PS with a molecular weight of 656.77 g/mol. The compound is classified as a nucleotide analog and is utilized in nucleic acid chemistry research.
Biological Activity I Assay Protocols (From Reference)
Targets
As a chemical reagent for oligonucleotide synthesis rather than a therapeutic drug, 2-O-DMT-Sulfonyldiethanol phosphoramidite does not have a defined biological target. Its role is in nucleic acid chemistry where it serves as a building block to introduce phosphorylated linkers into synthetic DNA or RNA sequences. The sulfonyldiethanol moiety provides a flexible spacer with a terminal hydroxyl group that can be further functionalized or phosphorylated.
ln Vitro
In cell-free biochemical systems, this phosphoramidite monomer is incorporated into oligonucleotide sequences during solid-phase synthesis. The resulting modified oligonucleotides containing the sulfonyldiethanol linker can be used in various molecular biology applications including affinity purification, surface immobilization, and probe labeling. The phosphorylated monomer enables the introduction of phosphate groups at specific positions within synthetic nucleic acid constructs for structural or functional studies.
ln Vivo
This compound does not exhibit intrinsic cellular activity as it is a chemical synthesis reagent rather than a biologically active drug. Its utility is confined to the in vitro synthesis of modified oligonucleotides that may subsequently be used in cell-based assays. The phosphoramidite is incorporated into oligonucleotide chains during automated synthesis, after which the resulting modified nucleic acids can be delivered into cells for various research applications including gene regulation studies, antisense experiments, and nucleic acid-based therapeutics development.
Enzyme Assay
The standard procedure for incorporating this phosphoramidite involves solid-phase oligonucleotide synthesis using standard phosphoramidite chemistry on controlled pore glass (CPG) or polystyrene supports. The monomer is dissolved in anhydrous acetonitrile at a concentration of approximately 0.1 M and coupled to the growing oligonucleotide chain using standard coupling reagents such as tetrazole or 5-ethylthio-1H-tetrazole. Coupling times typically range from 2-5 minutes. Following chain assembly, the oligonucleotide is deprotected and cleaved from the support using ammonium hydroxide treatment.
Cell Assay
No cell-based experimental protocols are applicable to this compound as it functions as a chemical synthesis reagent rather than a directly administered bioactive molecule. The compound is used exclusively in chemical synthesis workflows for the preparation of modified oligonucleotides. The resulting oligonucleotide products containing the sulfonyldiethanol modification can subsequently be evaluated in cell culture experiments to assess their biological activity, cellular uptake, stability, and functional effects in various cell lines depending on the specific application.
Animal Protocol
2-O-DMT-Sulfonyldiethanol phosphoramidite is not used in animal studies as it is a chemical intermediate rather than a drug substance. Oligonucleotides synthesized using this phosphoramidite may be evaluated in animal models for pharmacokinetic properties, biodistribution, and therapeutic efficacy. Typical animal studies involve intravenous, subcutaneous, or intraperitoneal administration of modified oligonucleotides in mice or rats at doses ranging from 1-50 mg/kg, with subsequent analysis of tissue distribution, target engagement, and pharmacological effects over time courses of hours to weeks.
ADME/Pharmacokinetics
As a chemical reagent used in oligonucleotide synthesis, this compound does not have established pharmacokinetic properties. The pharmacokinetic characteristics of oligonucleotides containing the sulfonyldiethanol modification would depend on the overall sequence length, backbone chemistry, and additional modifications present. Generally, modified oligonucleotides exhibit plasma half-lives ranging from several hours to days, with predominant clearance through nuclease degradation and renal excretion. Tissue distribution typically includes liver, kidney, and spleen with limited blood-brain barrier penetration.
Toxicity/Toxicokinetics
The compound is not intended for therapeutic use and therefore lacks established toxicity profiles. Standard laboratory safety precautions should be observed when handling this chemical reagent. The toxicity of oligonucleotides containing the sulfonyldiethanol modification would depend on the specific sequence and additional chemical modifications. Typical phosphorothioate-modified oligonucleotides show dose-limiting toxicities including immune stimulation, hepatotoxicity, and nephrotoxicity at high doses, with maximum tolerated doses varying from 10-100 mg/kg depending on the specific oligonucleotide chemistry and animal species.
Additional Infomation
2-O-DMT-Sulfonyldiethanol phosphoramidite is a research-grade chemical supplied for oligonucleotide synthesis applications. It is not an approved pharmaceutical and has no clinical trial history or regulatory status as a drug product. The compound is typically stored at -20°C under desiccated conditions to maintain stability and prevent hydrolysis of the phosphoramidite functionality. Purity specifications generally exceed 98% as determined by HPLC and 31P NMR analysis. This product is intended for research use only and is not for human or veterinary therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C34H45N2O7PS
Molecular Weight
656.77
Exact Mass
656.269
CAS #
108783-02-4
PubChem CID
10283145
Appearance
Colorless to light yellow liquid
LogP
7.8
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
19
Heavy Atom Count
45
Complexity
944
Defined Atom Stereocenter Count
0
SMILES
P(N(C(C)C)C(C)C)(OCCS(CCOC(C1=CC=C(OC)C=C1)(C1=CC=C(OC)C=C1)C1=CC=CC=C1)(=O)=O)OCCC#N
Synonyms
2-O-DMT-Sulfonyldiethanol phosphoramidite
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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 1.5226 mL 7.6130 mL 15.2260 mL
5 mM 0.3045 mL 1.5226 mL 3.0452 mL
10 mM 0.1523 mL 0.7613 mL 1.5226 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

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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