213743-12-5

Upstream product

• 78153-79-4 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl fluoride 
• 213743-11-4 ethyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside 
• 125411-99-6 ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 213743-10-3 ethyl 2,6-di-O-benzoyl-4,6-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 154391-05-6 2,3-di-O-benzoyl-1-ethylthio-β-D-galactopyranoside 
• 143838-81-7 ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 131564-36-8 ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 98-88-4 benzoyl chloride 
• 101966-50-1 2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride 

Downstream Products

• 213743-13-6 6-(Benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-galactopyranoside 
• 459844-80-5 (R)-glycidyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 459432-49-6 1-O-hexadecyl-3-O-[2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranosyl]-sn-glycerol 
• 459432-48-5 (R)-glycidyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line

Synthesis of three galactoglycerolipids (3-O-(β-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(α-D-galactopyranosyl-(1→4)-β-D-galactopyranosyl)-1-O- hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(α-D-galactopyranosyl-(1→4)-β-D-galactopyranosyl)-1-O- hexadecyl-sn-glycerol), and the corresponding glycerolipid (1-O-hexadecyl-2-O-palmitoyl-sn-glycerol) is described. The first two compounds were recently identified in the human colon carcinoma cell line HT29. The three-carbon synthon (S)-glycidol was used for construction of the glycerol moiety. Glycosylation of (S)-glycidol with protected galactosyl and digalactosyl donors produced galactosyl and digalactosyl glycidols. Lewis acid catalyzed opening of the epoxide produced protected galactosyl and digalactosyl glycerolipids. Deprotection, or palmitoylation followed by deprotection, yielded the target compounds. The corresponding glycerolipid was synthesized analogously and an oxidation-reduction procedure for tritiation was developed. The synthesized compounds will be used in studies of the role of galactosyl glycerolipids in differentiation and colon cancer development.

Chemoselective glycosylations of sterically hindered glycosyl acceptors

Unexpected intermolecular aglycon transfer in chemoselective glycosylations between activated thioglycosyl donors and deactivated thioglycosyl acceptors could be avoided by employing a glycosyl acceptor that has a bulky anomeric dicyclohexylmethanethio group. The methodology was applied to the synthesis of a protected fragment of an oligosaccharide released from the jelly coat glycoprotein of X. leavis.

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.