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566224

Sigma-Aldrich

3Fax-Peracetyl Neu5Ac

≥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

product name

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

Quality Level

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

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 Code

11 - Combustible Solids

WGK

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’.

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John Daly et al.
Blood advances, 6(11), 3352-3366 (2022-03-17)
Abnormal glycosylation is a hallmark of cancer, and the hypersialylated tumor cell surface facilitates abnormal cell trafficking and drug resistance in several malignancies, including multiple myeloma (MM). Furthermore, hypersialylation has also been implicated in facilitating evasion of natural killer (NK)
Bianca Saveria Fioretto et al.
Cells, 13(12) (2024-06-26)
Aberrant sialylation with overexpression of the homopolymeric glycan polysialic acid (polySia) was recently reported in fibroblasts from fibrotic skin lesions. Yet, whether such a rise in polySia levels or sialylation in general may be functionally implicated in profibrotic activation of
Bat-Erdene Jargalsaikhan et al.
Viruses, 16(6) (2024-06-27)
A gene delivery system utilizing lentiviral vectors (LVs) requires high transduction efficiency for successful application in human gene therapy. Pseudotyping allows viral tropism to be expanded, widening the usage of LVs. While vesicular stomatitis virus G (VSV-G) single-pseudotyped LVs are
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

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