KRN7000 - CAS 158021-47-7
Catalog number: 158021-47-7
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
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Description:
KRN7000 is a synthetic analog of α-galactosylceramide and the marine natural product agelasphin. It is a specific ligand for human and mouse NKT cells and remains the best studied ligand of the lipid-binding MHC class I-like protein CD1d. It protects against LPS-induced shock and displays potent antitumor activity in various in vivo models.
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Synonyms:
KRN7000; KRN-7000; KRN 7000; RGI-2001;
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Current Developer:
Regimmune Inc.
1.Synthesis of α-C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4'-epi-C-Glycoside of KRN7000.
Chang YJ1, Hsuan YC2, Lai AC1, Han YC1, Hou DR2. Org Lett. 2016 Feb 19;18(4):808-11. doi: 10.1021/acs.orglett.6b00090. Epub 2016 Feb 4.
A new immunostimulant, the 4'-epimer of α-C-GalCer, was synthesized from a C2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer.
2.Intramolecular nitrogen delivery for the synthesis of C-glycosphingolipids. Application to the C-glycoside of the immunostimulant KRN7000.
Altiti AS1, Mootoo DR. Org Lett. 2014 Mar 7;16(5):1466-9. doi: 10.1021/ol5002686. Epub 2014 Feb 21.
The key reaction in this approach to C-glycosphingolipids is the stereoselective iodocyclization of a sugar-linked homoallylic carbonimidothioate. E and Z reaction substrates were assembled in a convergent fashion via an alkene metathesis strategy and exhibited the same alkene facial selectivity in the iodocyclization irrespective of alkene geometry, although the E alkene was found to be less reactive.
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CAS 158021-47-7 KRN7000

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