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2F-Peracetyl-Fucose

Cat No.:V49168 Purity: ≥98%
2F-Peracetyl-Fucose (1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucopyranos) is a potent fucosyltransferase (fucosyltransferase; FUT) inhibitor.
2F-Peracetyl-Fucose
2F-Peracetyl-Fucose Chemical Structure CAS No.: 188783-78-0
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes
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Product Description
2F-Peracetyl-Fucose (1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucopyranos) is a potent fucosyltransferase (fucosyltransferase; FUT) inhibitor.
2F-Peracetyl-Fucose (CAS 188783-78-0), also known as 1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucopyranose, is a potent fucosyltransferase (FUT) inhibitor. It has a molecular weight of 292.26 g/mol and formula C12H17FO7. This fucosylated carbohydrate derivative is modified with acetyl groups at the hydroxyl positions and a fluorine atom at the 2-position. It inhibits protein fucosylation and is used in biochemical research to study fucosylation's role in inflammation, cell signaling, and microbial adhesion.
Biological Activity I Assay Protocols (From Reference)
Targets
2F-Peracetyl-Fucose targets fucosyltransferases (FUTs), enzymes that catalyze the transfer of fucose residues to acceptor molecules in glycoconjugate biosynthesis. Fucosylation is a critical post-translational modification involved in inflammation, cell signaling, microbial adhesion, and immune function. By inhibiting FUTs, 2F-Peracetyl-Fucose blocks protein fucosylation and allows researchers to study the role of fucosylation in various biological processes.
ln Vitro
2F-Peracetyl-Fucose is a potent fucosyltransferase (FUT) inhibitor. It inhibits fucosylation of IgG1 monoclonal antibodies produced by CHO-DG44 cells when used at a concentration of 50 µM. As a fucosylated carbohydrate derivative, it is used in biochemical research to study fucosylation's role in inflammation, cell signaling, and microbial adhesion. The compound is used in the analysis of substrate specificity and activity of glycosylases.
ln Vivo
In vivo activity data for 2F-Peracetyl-Fucose are not extensively detailed. As a fucosyltransferase inhibitor, it may have potential for modulating fucosylation-dependent processes in vivo. The compound is used in biochemical research employing both in vitro and in vivo experimental models to study fucosylation. Specific in vivo efficacy studies and animal model data are not specified in the public domain. The compound is intended for research use only.
Enzyme Assay
The in vitro enzyme assay for 2F-Peracetyl-Fucose typically involves measuring the inhibition of fucosyltransferase (FUT) enzymatic activity. Recombinant FUT enzymes are incubated with varying concentrations of 2F-Peracetyl-Fucose (typically 0.1-1000 µM) in the presence of a fucose donor (GDP-fucose) and an acceptor substrate. The enzymatic activity is measured by monitoring the transfer of fucose to the acceptor using radiometric, fluorescence, or mass spectrometry-based methods. The compound is dissolved in DMSO or water and diluted in assay buffer.
Cell Assay
In vitro cellular assays for 2F-Peracetyl-Fucose typically involve treating cells with the compound at concentrations ranging from 1 to 100 µM for various time periods. Protein fucosylation is assessed by lectin blotting using fucose-specific lectins (such as AAL or UEA-I) or by mass spectrometry. Cell surface fucosylation is assessed by flow cytometry. The compound's effects on cell signaling, inflammation, and adhesion are assessed using standard assays. The compound is dissolved in DMSO and diluted in cell culture medium.
Animal Protocol
In vivo animal studies for 2F-Peracetyl-Fucose are not extensively documented. For potential in vivo applications, the compound could be administered to mice via oral gavage or intraperitoneal injection at doses determined from preliminary studies. Fucosylation levels in tissues are assessed by lectin blotting or mass spectrometry. The compound's effects on inflammation, immune responses, and microbial adhesion are evaluated in appropriate disease models.
ADME/Pharmacokinetics
2F-Peracetyl-Fucose has a molecular weight of 292.26 g/mol and formula C12H17FO7. Purity is typically >99.99%. Recommended storage is at -20°C. The compound is soluble in DMSO and other organic solvents. Detailed PK parameters such as half-life, Cmax, AUC, and bioavailability would require experimental determination. The compound is a fucosylated carbohydrate derivative with acetyl groups at the hydroxyl positions.
Toxicity/Toxicokinetics
2F-Peracetyl-Fucose is intended for research use only and is not approved for human therapeutic applications. As a fucosyltransferase inhibitor, the compound may affect normal fucosylation-dependent processes, which could contribute to potential toxicity. Standard preclinical toxicity assessments would include acute toxicity studies in rodents, repeated-dose toxicity studies, and assessment of off-target effects. Appropriate safety precautions should be taken when handling.
References

[1]. Impact of Acetylated and Non-Acetylated Fucose Analogues on IgG Glycosylation. Antibodies (Basel). 2019 Jan 10;8(1):9.

Additional Infomation
2F-Peracetyl-Fucose (CAS 188783-78-0) is a potent fucosyltransferase (FUT) inhibitor with a molecular weight of 292.26 g/mol and formula C12H17FO7. It is also known as 1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucopyranose. The compound inhibits protein fucosylation and is used in biochemical research to study fucosylation's role in inflammation, cell signaling, and microbial adhesion. It is not approved for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H17FO7
Molecular Weight
292.257588148117
Exact Mass
292.096
CAS #
188783-78-0
PubChem CID
18661011
Appearance
White to off-white solid powder
LogP
0.495
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
6
Heavy Atom Count
20
Complexity
397
Defined Atom Stereocenter Count
4
SMILES
C[C@H]1[C@H]([C@H]([C@@H](C(O1)OC(=O)C)F)OC(=O)C)OC(=O)C
InChi Key
QFVJLBVULJFLKN-VLCHEQJQSA-N
InChi Code
InChI=1S/C12H17FO7/c1-5-10(18-6(2)14)11(19-7(3)15)9(13)12(17-5)20-8(4)16/h5,9-12H,1-4H3/t5-,9-,10+,11-,12?/m0/s1
Chemical Name
[(2S,3R,4R,5S)-4,6-diacetyloxy-5-fluoro-2-methyloxan-3-yl] acetate
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)
DMSO : ~100 mg/mL (~342.16 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.4216 mL 17.1081 mL 34.2161 mL
5 mM 0.6843 mL 3.4216 mL 6.8432 mL
10 mM 0.3422 mL 1.7108 mL 3.4216 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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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)
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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