Skip to Content
MilliporeSigma
All Photos(2)

Documents

566224

Sigma-Aldrich

Sialyltransferase Inhibitor, 3Fax-Peracetyl Neu5Ac

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

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C22H30FNO14
Molecular Weight:
551.47
UNSPSC Code:
12352200

Quality Level

100

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 4

1 of 4

PR-619 ≥95% (HPLC)

Sigma-Aldrich

SML0430

PR-619

Cobalt(II) chloride purum p.a., anhydrous, ≥98.0% (KT)

Sigma-Aldrich

60818

Cobalt(II) chloride

Neuraminidase (Sialidase) from Arthrobacter ureafaciens

Roche

10269611001

Neuraminidase (Sialidase)

PhosSTOP™ sufficient for 10 10mL buffer preparations, sufficient for 20 10mL buffer preparations, suitable for tissue processing, suitable for immunoprecipitation (IP)

Roche

PHOSS-RO

PhosSTOP™

Marlieke L M Jongsma et al.
Immunity, 54(1), 132-150 (2020-12-04)
HLA class I (HLA-I) glycoproteins drive immune responses by presenting antigens to cognate CD8+ T cells. This process is often hijacked by tumors and pathogens for immune evasion. Because options for restoring HLA-I antigen presentation are limited, we aimed to identify

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service