221344-11-2

Upstream product

• 221344-09-8 (1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 231278-92-5 (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester 
• 51096-08-3 (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid 
• 145240-79-5 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite 
• 144002-21-1 dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite 

Downstream Products

• 566942-88-9 C₆₂H₉₀N₂O₃₄ 

Relevant academic research and scientific papers

Synthesis of a pseudo tetrasaccharide mimic of ganglioside GM1

The pseudo tetrasaccharide 2 was designed to mimic ganglioside GM1, the membrane receptor of both the cholera toxin and of the heat-labile toxin of E. coli. Compound 2 retains the Gal and Neu5Ac recognition determinant of GM1 and uses as the scaffold elem

Sugar mimics: An artificial receptor for cholera toxin

The paper describes the pseudosugar 2 [Galβ1-3GalNAcβ1-4(NeuAcα2- 3)DCCHD], a high affinity binder of cholera toxin (CT). The molecule was designed using molecular modeling techniques to mimic the natural CT membrane receptor, ganglioside GM1. The central residue of GM1, a 3,4-disubstituted galactose unit, was recognized as the ganglioside scaffold element and substituted with a conformationally locked cyclohexanediol (DCCHD). DCCHD was synthesized in enantiopure form using enantioselective Diels Alder methodology and regioselectively α-sialylation at the equatorial position. Glycosylation with a Galβ(1-3)-GalNAc donor completed the synthesis of 2. The solution structure of 2 and its binding ability to CT were found to be analogous to those of the GM1 oligosaccharide.