1309668-41-4

Upstream product

• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 
• 506-46-7 1-hexacosanoic acid 
• 53081-30-4 tetra-O-benzyl-α-D-galactosyl bromide 
• 1309668-42-5 (2R,4R)-2-azido-4-(benzyloxy)octadecan-1-ol 
• 1309668-40-3 N-((2R,4R)-4-(benzyloxy)-1-hydroxyoctadecan-2-yl)hexacosanamide 
• 101966-50-1 2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride 
• 1309668-39-0 (2R,4R)-2-amino-4-(benzyloxy)octadecan-1-ol 
• 1309668-37-8 ((2S,3R,4R)-2-azido-4-(benzyloxy)-3-bromooctadecyloxy)(tert-butyl)diphenylsilane 
• 1057620-74-2 C₂₅H₄₃N₃O₃ 
• 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 
• 1233216-85-7 (2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol 

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.