1233216-85-7

Upstream product

• 1057620-74-2 C₂₅H₄₃N₃O₃ 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 1309668-43-6 (2S,3R,4S,5S,6R)-2-((2R,4R)-2-azido-4-(benzyloxy)octadecyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran 
• 1309668-37-8 ((2S,3R,4R)-2-azido-4-(benzyloxy)-3-bromooctadecyloxy)(tert-butyl)diphenylsilane 
• 1309668-39-0 (2R,4R)-2-amino-4-(benzyloxy)octadecan-1-ol 
• 1309668-40-3 N-((2R,4R)-4-(benzyloxy)-1-hydroxyoctadecan-2-yl)hexacosanamide 
• 1309668-41-4 N-((2R,4R)-4-(benzyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)hexacosanamide 
• 1309668-42-5 (2R,4R)-2-azido-4-(benzyloxy)octadecan-1-ol 
• 1233216-84-6 (4R,E)-2-azido-4-O-benzyl-1-O-tert-butyldiphenylsilyl-octadec-2-ene-1,4-diol 

Relevant academic research and scientific papers

The 3-deoxy analogue of α-GalCer: Disclosing the role of the 4-hydroxyl group for CD1d-mediated NKT Cell activation

KRN7000, or α-GalCer, is a potent agonist for natural killer T (NKT) cells. The 3-hydroxyl group of its phytosphingosine moiety is important for activating NKT cells, whereas its 4-hydroxyl group is perceived to be less crucial. To experimentally determine the role of the 4-hydroxyl group, we synthesized the 3-deoxy analogue of α-GalCer. It was found that 3-deoxy-α-GalCer induced potent cytokine responses from NKT cells, comparable to those of both α-GalCer and 4-deoxy-α-GalCer. This result and our docking studies suggest that the effects of an absence of the 3-hydroxyl group are compensated by the presence of a hydroxyl group at the C-4 position. Thus, we conclude that the 4-hydroxyl group of α-GalCer is as important to the mechanism of action as the 3-hydroxyl group and that the two hydroxyl groups could play individual and cooperative roles in orienting the glycolipid into the proper position in CD1d to be recognized by the T cell receptor of NKT cells.