155835-94-2Relevant academic research and scientific papers
Regioselective acylation of diols and triols: The cyanide effect
Peng, Peng,Linseis, Michael,Winter, Rainer F.,Schmidt, Richard R.
supporting information, p. 6002 - 6009 (2016/06/09)
Central topics of carbohydrate chemistry embrace structural modifications of carbohydrates and oligosaccharide synthesis. Both require regioselectively protected building blocks that are mainly available via indirect multistep procedures. Hence, direct pr
Potential use of synthetic α-galactosyl-containing glycotopes of the parasite Trypanosoma cruzi as diagnostic antigens for Chagas disease
Ashmus, Roger A.,Schocker, Nathaniel S.,Cordero-Mendoza, Yanira,Marques, Alexandre F.,Monroy, Erika Y.,Pardo, Andrew,Izquierdo, Luis,Gállego, Montserrat,Gascon, Joaquim,Almeida, Igor C.,Michael, Katja
, p. 5579 - 5583 (2013/09/12)
A synthetic glycoarray containing non-reducing α-galactopyranosyl moieties related to mucin O-glycans of the parasite Trypanosoma cruzi was evaluated by a chemiluminescent enzyme-linked immunosorbent assay with sera from patients with chronic Chagas disease. Our data revealed the disaccharide Galα(1,3)Galβ as the immunodominant glycotope, which may eventually be employed as a diagnostic antigen for Chagas disease.
Synthesis of oligosaccharides related to the HNK-1 antigen: I. Synthesis of selectively protected allyl 3-O-[methyl(β-D-glucopyranosyl)uronate]-β-D-galactopyranoside
Kornilov,Kononov,Zatonskii,Shashkov,Nifant'ev
, p. 597 - 607 (2007/10/03)
The glycosylation of several mono- and dihydroxyl glycosyl acceptors based on allyl β-D-galactopyranoside with completely acylated glucuronyl bromides under the Helferich reaction conditions was studied in order to develop a method for the preparative synthesis of selectively protected disaccharide β-D-GlcA-(1→3)-β-D-Gal in a form that can be used for further preparation of corresponding glycosyl donors and spacerated derivatives. We found that 1,2-orthoesters were the major primary products of the reaction, and their further conversion into isomeric glycosides depended on pH and can be regulated by the type of molecular sieves used. When Acid Washed Molecular Sieves AW 300 were used, glycosides were predominantly synthesized. No selective formation of the (1→3)-bound disaccharide was observed upon glycosylation of glycosyl acceptors with 2,3- and 3,4-diol groupings. This (1→3)-bound disaccharide was most efficiently synthesized by glycosylation of allyl 4,6-O-benzylidene-2-O-benzoyl-β-D-galactopyranoside with pivaloylated glucuronyl bromide. With acetylated or benzoylated glucuronyl bromides or with pivaloyl glucuronyl imidate, this galactoside can also be glycosylated but with a lower yield of the target (1→3)-bound disaccharide and lower glycosylation regioselectivity.
Synthesis of allyl 3-deoxy- and 4-deoxy-β-D-galactopyranoside and simultaneous preparations of Gal(1 → 2)- and Gal(1 → 3)-linked disaccharide glycosides
Lee,Lee
, p. 69 - 79 (2007/10/02)
Syntheses of galactose derivatives that are useful in probing the binding specificity of galactose-specific lectins are reported. These include allyl 3-deoxy- and 4-deoxy-β-D-xylo-hexopyranoside and several disaccharide glycosides having Gal(1 → 2) and Gal(1 → 3) linkages. The β-linked Gal disaccharide isomers were produced using 2,3,4,6-tetra-O-acetyl-α-D- galactopyranosyl bromide as glycosyl donor and the 4,6-O-benzylidene derivatives of allyl β-D-galactopyranoside, α-D-glucopyranoside, α-D- mannopyranoside, and 2-acetamido-2-deoxy-α-D-galactopyranoside as acceptors. Only the Gal(1 → 3)-linked disaccharide was obtained when the benzylidene derivatives of the mannopyranoside and 2-acetamido-2-deoxygalactopyranoside were used. Attempts at the preparation of Gal(α, 1 → 2)Gal and Gal(α, 1 → 3)Gal disaccharide glycosides were made using the same strategy, but employing the 1-trichloro-acetimidate or 1-N-methylacetimidate of 2,3,4,6- tetra-O-benzyl-D-galactopyranose as the glycosyl donor. The latter imidate produced a mixture of Gal(α, 1 → 2)Gal and Gal(α, 1 → 3)Gal derivatives as major products, but the former gave the Gal(β, 1 → 2)Gal isomer as the major product. Syntheses of galactose derivatives that are useful in probing the binding specificity of galactose-specific lectins are reported. These include allyl 3-deoxy- and 4-deoxy-β-D-xylo-hexophyranoside and several disaccharide glycosides having Gal(a→2)Gal and Gal(1→3) linkages. The β-linked Gal disaccharide isomers were produced using 2,3,4,6-tetra-O- acetyl-α-D-galactopyronosyl bromide as glycosyl donor and the 4,6-O-benzylidene deriatives of allyl β-D-galactopyranoside, α-D-glucopyranoside, α-D-manopyranoside, and 2-acetamido-2-deoxy-α-D-galactopyranoside as acceptors. Only the Gal(2→3)-linked disaccharide was obtained when the benzylidene derivatives of the mannopyranosde and 2-acetamido-2-deoxygalactopyranoside were used. Attempts at the preparation of Gal(α, 1→2)Gal and Gal(α, 1→3)Gal disaccharide glycosides were made using the same strategy, but employing the 1-trichloroacetimidate or 1-N-methylacetimidate of 2,3,4,6-tetra-O-benzyl-D-galactopyranose as the glycosyl donor. The latter imidate produced a mixture of Gal(α, 1→2)Gal and Gal(α, 1→3)Gal derivatives as major products, but the former gave the Gal(β, 1→2)Gal isomer as the major product.
