496019-46-6

Upstream product

• 4163-60-4 β-D-galactose peracetate 
• 167612-33-1 (2R,6S,7R,8R,8aR)-2-phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 
• 100-39-0 benzyl bromide 
• 108-98-5 thiophenol 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 

Downstream Products

• 38184-12-2 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 144781-45-3 phenyl 2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 938176-22-8 (2S,3S,4R)-1-(((2R,6S,7R,8S,8aS)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]-dioxin-6-yl)oxy)-2-((tert-butoxycarbonyl)amino)octadecane-3,4-diyl dibenzoate 
• 905928-15-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2S,3S,4R)-3,4-bis (benzoyloxy)-2-((tert-butoxycarbonyl)amino)octadecyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 496019-53-5 phenyl 2,3,4-tri-O-benzyl-6-{2-[ω-hydroxy-penta-(oxyethylen)ethyl]}-1-thio-β-D-galactopyranoside 
• 496019-49-9 phenyl 2,3,6-tri-O-benzyl-4-{2-[ω-hydroxy-penta-(oxyethylen)ethyl]}-1-thio-β-D-galactopyranoside 
• 496019-48-8 phenyl 2,3,6-tri-O-benzyl-4-{2-[ω-hydroxy-tetra-(oxyethylen)ethyl]}-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Optical Control of Cytokine Production Using Photoswitchable Galactosylceramides

α-Galactosylceramides are glycosphingolipids that show promise in cancer immunotherapy. After presentation by CD1d, they activate natural killer T cells (NKT), which results in the production of a variety of pro-inflammatory and immunomodulatory cytokines. Herein, we report the synthesis and biological evaluation of photochromic derivatives of KRN-7000, the activity of which can be modulated with light. Based on established structure–activity relationships, we designed photoswitchable analogues of this glycolipid that control the production of pro-inflammatory cytokines, such as IFN-γ. The azobenzene derivative α-GalACer-4 proved to be more potent than KRN-7000 itself when activated with 370 nm light. Photolipids of this type could improve our mechanistic understanding of cytokine production and could open new directions in photoimmunotherapy.