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D-(+)-Fucose (D-fucose)

Cat No.:V61993 Purity: ≥98%
D-(+)-Fucose is a non-metabolized analog of l-arabinose.
D-(+)-Fucose (D-fucose)
D-(+)-Fucose (D-fucose) Chemical Structure CAS No.: 3615-37-0
Product category: Saccharides
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
D-(+)-Fucose is a non-metabolized analog of l-arabinose. D-(+)-Fucose prevents the growth of E. coli B/r on mineral salt medium plus l-arabinose by inhibiting the induction of l-arabinose operon. D-(+)-Fucose is a potent inducer of β-methylgalactoside transdermal enzyme (MGP).
D-(+)-Fucose (CAS 3615-37-0) is a monosaccharide and the D-enantiomer of L-fucose, also known as aldehyde-D-fucose. It has the molecular formula C₆H₁₂O₅ and a molecular weight of 164.16 g/mol. D-(+)-Fucose is a non-metabolizable analog of L-arabinose. It inhibits the induction of the L-arabinose operon and prevents the growth of Escherichia coli B/r on mineral salts medium with L-arabinose. The compound is involved in cell-cell recognition, immune response modulation, inflammation regulation, and is a key component of fucosylated oligosaccharides in human milk. It is used to increase the yield and activity of recombinant proteins and is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
L-arabinose operon; β-methylgalactoside permease. D-(+)-Fucose is a non-metabolizable analog of L-arabinose that inhibits the induction of the L-arabinose operon and prevents the growth of E. coli on L-arabinose. It is an inducer of β-methylgalactoside permease. The compound is involved in cell-cell recognition, immune response modulation, and inflammation regulation through its incorporation into glycoproteins and glycolipids.
ln Vitro
D-(+)-Fucose inhibits the induction of the L-arabinose operon and prevents the growth of Escherichia coli B/r on mineral salts medium with L-arabinose. It is a non-metabolizable analog of L-arabinose and an inducer of β-methylgalactoside permease. The compound is involved in cell-cell recognition, immune response modulation, and inflammation regulation and is used to increase the yield and activity of recombinant proteins.
ln Vivo
In vivo, D-(+)-fucose is involved in immune response modulation, inflammation regulation, and cell-cell recognition. It is a key component of fucosylated oligosaccharides in human milk, contributing to gut health and infant immunity. The compound is used to increase the yield and activity of recombinant proteins in expression systems. It is not administered as a therapeutic agent but serves as a research tool for studying carbohydrate metabolism and cell signaling.
Enzyme Assay
Non-cell-based assays for D-(+)-fucose include bacterial growth inhibition assays using E. coli B/r cultures grown on mineral salts medium with L-arabinose. The compound’s ability to inhibit growth is measured by optical density. β-Methylgalactoside permease induction assays can be performed using bacterial cultures. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization and purity assessment.
Cell Assay
Cell-based assays for D-(+)-fucose use bacterial cultures (E. coli) to assess inhibition of the L-arabinose operon. Mammalian cell culture models can be used to study the compound’s effects on cell-cell recognition, immune response modulation, and inflammation regulation. The compound’s incorporation into glycoproteins and glycolipids can be assessed using metabolic labeling techniques.
Animal Protocol
In vivo studies of D-(+)-fucose are conducted in animal models to study its effects on immune response modulation, inflammation regulation, and cell-cell recognition. The compound is a key component of human milk oligosaccharides and is studied for its role in gut health and infant immunity. Standard protocols for these models involve administration of the compound followed by measurement of relevant endpoints.
ADME/Pharmacokinetics
D-(+)-Fucose has a molecular formula of C₆H₁₂O₅ and a molecular weight of 164.16 g/mol. Purity is ≥97%. It is a monosaccharide and the D-enantiomer of L-fucose. The compound is a non-metabolizable analog of L-arabinose and should be stored under recommended conditions. It is intended for research use only.
Toxicity/Toxicokinetics
D-(+)-Fucose is generally considered to have low toxicity. Standard laboratory safety practices should be followed when handling this compound.
References

[1]. D-Fucose as a gratuitous inducer of the L-arabinose operon in strains of Escherichia coli B-r mutant in gene araC. J Bacteriol. 1971;107(1):79-86.

Additional Infomation
Aldehyde-D-fucose is both D-fucose and aldehyde-fucose. It is the enantiomer of aldehyde-L-fucose.
D-(+)-Fucose is a monosaccharide and the D-enantiomer of L-fucose. It is a non-metabolizable analog of L-arabinose that inhibits the induction of the L-arabinose operon and prevents the growth of E. coli on L-arabinose. It is an inducer of β-methylgalactoside permease and is involved in cell-cell recognition, immune response modulation, and inflammation regulation. It is a key component of fucosylated oligosaccharides in human milk and is used to increase the yield and activity of recombinant proteins. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H12O5
Molecular Weight
164.16
Exact Mass
164.068
CAS #
3615-37-0
PubChem CID
94270
Appearance
White to off-white solid powder
Density
1.41 g/cm3
Boiling Point
399.1ºC at 760 mmHg
Melting Point
144-145ºC(lit.)
Flash Point
209.3ºC
Index of Refraction
75.5 ° (C=10, H2O)
LogP
-2.4
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
4
Heavy Atom Count
11
Complexity
126
Defined Atom Stereocenter Count
4
SMILES
C[C@H]([C@@H]([C@@H]([C@H](C=O)O)O)O)O
InChi Key
PNNNRSAQSRJVSB-DPYQTVNSSA-N
InChi Code
InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4+,5+,6-/m1/s1
Chemical Name
(2R,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanal
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)
H2O: 250 mg/mL (1522.90 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (609.16 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.0916 mL 30.4581 mL 60.9162 mL
5 mM 1.2183 mL 6.0916 mL 12.1832 mL
10 mM 0.6092 mL 3.0458 mL 6.0916 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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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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