alpha-Mannosylceramide
| Code | Size | Price |
|---|
| AG-CR1-3594-C250 | 250 ug | £130.00 |
Quantity:
| AG-CR1-3594-M001 | 1 mg | £260.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
-20°C
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
alpha-ManCer; alpha-Mannosyl Ceramide; (2S,3S,4R)-2-Amino-N-hexacosanoyl-1-O-(alpha-D-mannopyranosyl)-1,3,4-octadecanetriol; alpha-D-Galactopyranoside
Appearance:
White to off-white solid.
CAS:
320610-63-7
EClass:
32160000
Form (Short):
liquid
Handling Advice:
After reconstitution, prepare aliquots and store at -20°C.Aliquot into glass vials.
InChi:
InChI=1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49-,50-/m0/s1
InChiKey:
VQFKFAKEUMHBLV-CIKDURTISA-N
Long Description:
Chemical. CAS: 320610-63-7. Formula: C50H99NO9. MW: 858.3. Potent stimulator of natural killer T (NKT) cells expressing the invariant Valpha19-Jalpha26 T cell receptor alpha chain (Valpha19 NKT cells).
Molecular Formula:
C50H99NO9
Molecular Weight:
858.3
Other 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 alpha-chain and a somewhat variable beta-chain. The majority of NKT cells express the invariable alpha-chain Valpha14-Jalpha18 (Valpha14) in mouse or its homolog in humans Valpha24-Jalpha18 (Valpha24). Valpha14 NKT cells recognize alpha-GalCer presented by CD1d. NKT cells expressing the invariant Valpha19-Jalpha26 TCR alpha-chain (Valpha19 NKT cells) have been found in peripheral blood lymphocytes and in the liver. They recognize alpha-ManCer presented by MR1 (Major histocompatibility complex, class I-related) and respond with production of large amounts of immunoregulatory cytokines.
Package Type:
Vial
Product Description:
Potent stimulator of natural killer T (NKT) cells expressing the invariant Valpha19-Jalpha26 T cell receptor alpha chain (Valpha19 NKT cells).
Purity:
>95% (TLC)
SMILES:
CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COC1OC(CO)C(O)C(O)C1O)[C@H](O)[C@H](O)CCCCCCCCCCCCCC
Solubility Chemicals:
Soluble in pyridine or warm DMSO.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
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)