α-Mannosylceramide

Specifications / Handling

More Information
Product Details
Synonyms	α-ManCer; α-Mannosyl Ceramide; (2S,3S,4R)-2-Amino-N-hexacosanoyl-1-O-(α-D-mannopyranosyl)-1,3,4-octadecanetriol; α-D-Galactopyranoside
Product Type	Chemical
Properties
Formula	C₅₀H₉₉NO₉
MW	858.3
CAS	320610-63-7
Purity Chemicals	≥95% (TLC)
Appearance	White to off-white solid.
Solubility	Soluble in pyridine or warm DMSO.
Other Product Data	Natural killer T cells (NKT cells) are important regulators of the immune system. They share properties of both innate as well as adaptive immunity. They express T cell receptors (TCR) on their surface consisting of an invariable α-chain and a somewhat variable β-chain. The majority of NKT cells express the invariable α-chain Vα14-Jα18 (Vα14) in mouse or its homolog in humans Vα24-Jα18 (Vα24). Vα14 NKT cells recognize α-GalCer presented by CD1d. NKT cells expressing the invariant Vα19-Jα26 TCR α-chain (Vα19 NKT cells) have been found in peripheral blood lymphocytes and in the liver. They recognize α-ManCer presented by MR1 (Major histocompatibility complex, class I-related) and respond with production of large amounts of immunoregulatory cytokines.
InChi Key	VQFKFAKEUMHBLV-CIKDURTISA-N
Smiles	CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COC1OC(CO)C(O)C(O)C1O)[C@H](O)[C@H](O)CCCCCCCCCCCCCC
Shipping and Handling
Shipping	BLUE ICE
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	After reconstitution, prepare aliquots and store at -20°C. Aliquot into glass vials.
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

Product-specific References

Description

Potent stimulator of natural killer T (NKT) cells expressing the invariant Vα19-Jα26 T cell receptor α chain (Vα19 NKT cells).

Product References

CD1d-restricted and TCR-mediated activation of valpha14 NKT cells by glycosylceramides: T. Kawano, et al.; Science 278, 1626 (1997)
Synthetic alpha-mannosyl ceramide as a potent stimulant for an NKT cell repertoire bearing the invariant Valpha19-Jalpha26 TCR alpha chain: N. Okamoto, et al.; Chem. Biol. 12, 677 (2005)
MR1-restricted Valpha19i T cells: a second population recognizing lipid antigens?: J. Schumann & G. De Libero; Eur. J. Immunol. 37, 1724 (2007)
Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Valpha19 NKT cell with alpha-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit: M. Shimamura, et al.; Eur. J. Med. Chem. 41, 569 (2006)
Modulation of Valpha19 NKT cell immune responses by alpha-mannosyl ceramide derivatives consisting of a series of modified sphingosines: M. Shimamura, et al.; Eur. J. Immunol. 37, 1836 (2007)
Glycolipid stimulators for NKT cells bearing invariant V alpha 19-J alpha 33 TCR alpha chains: M. Shimamura; MiniRev. Med. Chem. 8, 285 (2008)
Non-reducing end alpha-mannosylated glycolipids as potent activators for invariant Valpha19 TCR-bearing natural killer T cells: M. Shimamura; Carbohydr. Res. 343, 2010 (2008)

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