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566224

3Fax-Peracetyl Neu5Ac

Name: 3Fax-Peracetyl Neu5Ac
Brand: MM

≥98% (NMR), solid, sialytransferase inhibitor, Calbiochem^®

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

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₃₀FNO₁₄

Molecular Weight:

551.47

UNSPSC Code:

12352200

NACRES:

NA.54

Assay:

≥98% (HPLC)

Form:

solid

Storage condition:

OK to freeze, protect from light

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Properties

Product Name

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

Quality Segment

100

assay

≥98% (HPLC)

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

Description

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 SLe^X 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

Preparation Note

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c