117606-38-9

Upstream product

• 27891-73-2 β-phenylsulfanyl lactoside 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 117606-41-4 phenyl O-(6-O-benzoyl-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 117606-40-3 C₄₃H₆₆O₁₅S 
• 213743-04-5 Phenyl 2,3-di-O-benzoyl-4,6-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 117606-39-0 phenyl O-(4,6-di-O-isopropylidene-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-pivaloyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Chemical synthesis of globotriose and galabiose: Relative stabilities of their complexes with Escherichia coli Shiga-like toxin-1 as determined by denaturation-titration with guanidinium chloride

Globotriose [α-D-Gal-(1→4)-β-D-Gal-(1→4)-D-Glc] is the carbohydrate moiety of the globotriosyl ceramide (Gb3), also known as the germinal centre B-cell differentiation antigen CD77, a glycolipid present on the plasma membrane of certain mammalian cells. In Gb3, globotriose functions as the cell-surface receptor for Shiga toxin and for the Shiga-like toxins (verocytotoxins). Here we report the chemical synthesis of globotriose and the corresponding terminal disaccharide, galabiose [α-D-Gal-(1→4)-β-D-Gal]. Globotriose and galabiose are attached via a linker to CNBr-activated Sepharose to generate affinity matrices that permit the one-step purification of recombinant Shiga-like toxin-1 from crude E. coli homogenates. Toxin is released from either of the immobilised saccharides by elution with 6 M guanidinium chloride. After dilution of the denaturant, the released toxin had full catalytic activity. Denaturation-titration experiments show that the bound toxin is released from galabiose-Sepharose at 2.3 M guanidinium chloride, while its release from globotriose-Sepharose requires a higher concentration of 4.8 M. These results indicate that the glucose component of globotriose contributes ～2.6 kcal mol-1 to the binding energy relative to galabiose.

Total synthesis of globotriaosylceramide (Gb3) and lysoglobotriaosylceramide (lysoGb3)

We have recently reported a highly efficient and stereocontrolled synthesis of globotriaosylceramide (Gb3, 1) in optically pure form.Key to our synthetic strategy was the implementation of the two-stage activation of thioglycosides for formatio