α-Galactosylceramide (Dansylated)

CHF 590.00
In stock
AG-CN2-0514-M0011 mgCHF 590.00
More Information
Product Details
Synonyms α-Gal-Cer (Dansylated); KRN7000 (Dansylated)
Product Type Chemical
Properties
Formula

C62H111N3O10S

MW 1090.6
CAS 424823-23-4
Purity Chemicals ≥95% (1H-NMR, 13C-NMR and TLC (CH2Cl2/MeOH 3:1)
Appearance Off-white solid.
Solubility Soluble in pyridine and DMSO.
Identity Identity determined by 1H-NMR and MS.
Other Product Data

NOTE: This glycolipid compound can be challenging in terms of solubility. For further information on solubility of this compound, please refer to J.M.H. Cheng, et al.; Carbohydr. Res. 346, 914 (2011), Experimental Section 4.16.2.

InChi Key IANVHCHZQVOSSG-FWGSTNQDSA-N
Smiles O[C@H]1[C@@H](O)[C@@H](CNS(C2=CC=CC3=C2C=CC=C3N(C)C)(=O)=O)O[C@H](OC[C@@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=O)[C@@H]1O
Shipping and Handling
Shipping BLUE ICE
Short Term Storage -20°C
Long Term Storage -20°C
Handling Advice Aliquot into glass vials.
Keep cool and dry.
Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Fluorescent α-GalCer derivative.
  • Potent stimulator of invariant natural killer T (iNKT) cells similar to α-GalCer (determined by CD86 expression in DCs and B cells, and IL-2 production by iNKT cells). Specific ligand of the lipid-binding MHC class I-like protein CD1d in human and mouse NKT cells.
  • Used as a fluorescent marker for the uptake of the glycolipid by dendritic cells (DC's) in vitro and to better understand the mechanism of iNKT cell activation.
    Product References
    1. Synthesis and NKT cell stimulating properties of fluorophore- and biotin-appended 6''-amino-6''-deoxy- galactosylceramides: X.-T. Zhou, et al.; Org. Lett. 4, 1267 (2002)
    2. An improved synthesis of dansylated alpha-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells: J.M.H. Cheng, et al.; Carbohydr. Res. 346, 914 (2011)
    3. Trehalose diesters, lipoteichoic acids and alpha-GalCer: using chemistry to understand immunology: B.L. Stocker & M.S.M. Timmer; Carbohydr. Res. 389, 3 (2014)
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