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Sigma-Aldrich

Sialyltransferase Inhibitor, 3Fax-Peracetyl Neu5Ac

The Sialyltransferase Inhibitor, 3Fax-Peracetyl Neu5Ac controls the biological activity of Sialyltransferase.

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Synonym(s):
Sialyltransferase Inhibitor, 3Fax-Peracetyl Neu5Ac, (1S,2R)-1-((3S,4R,5R,6S)-3-acetamido-4,6-diacetoxy-5-fluoro-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate, 3F ax-Neu5Ac Prodrug
Empirical Formula (Hill Notation):
C22H30FNO14
Molecular Weight:
551.47

Quality Level

assay

≥98% (NMR)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 50 mg/mL

shipped in

ambient

storage temp.

−70°C

SMILES string

F[C@@H]1[C@@H]([C@H](C([C@@H]([C@@H](COC(C)=O)OC(C)=O)OC(C)=O)OC(C(OC)=O)1OC(C)=O)NC(C)=O)OC(C)=O

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Akt Inhibitor III

vibrant-m

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STAT3 Inhibitor XVI

assay

≥98% (NMR)

assay

≥98% (NMR)

assay

≥98% (NMR)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

storage temp.

−70°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

DMSO: 50 mg/mL

solubility

DMSO: 10 mg/mL

solubility

DMSO: 10 mg/mL

solubility

DMSO: 50 mg/mL, light pink-purple

General description

A cell-permeable sialylic acid analog that upon cellular uptake is transformed into a CMP-Neu5Ac (a href="http://www.emdmillipore.com/products/EMD_BIO-233264" target=_blank>233264) mimetic bearing a C3 fluorine substituent at the axial position, effectively inhibiting sialyltransferase in a donor substrate CMP-Neu5Ac-competitive manner. Shown to effectively abloishes HL-60 cell surface SLeX expression (by >95%; 200 µM for 5 days), resulting in dramatic reductions in cell surface E-selectin and P-selectin binding (by >95% and >80%, respectively), without affecting cell viability or proliferation.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Sialyltransferase
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -70°C.

Other Notes

Rillahan, C., et al. 2012. Nat. Chem. Bio.8, 661.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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