Practical synthesis of fully protected globotriaose and its glycopolymers

Matsuoka, Koji; Goshu, Yusuke; Takezawa, Yutaka; Mori, Takeo; Sakamoto, Junichi; Yamada, Akihiro; Onaga, Tomotsune; Koyama, Tetsuo; Hatano, Ken; Snyder, Philip W.; Toone, Eric J.; Terunuma, Daiyo

doi:10.1016/j.carbpol.2006.10.011

Cited by 17 publications

(6 citation statements)

References 26 publications

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“…Briefly, pulmonary trisaccharide 2 was synthesized by the coupling of N -trichloroacetyl-protected GalNAc donor 10 with lactose-derived acceptor 11 and N -iodosuccinimide-triflic acid activation conditions, yielding the desired β-glycoside 12 in 86% yield (Scheme , see Experimental Procedures section for details). Reductive dechlorination with tributyltin hydride, followed by methanolic deacetylation and global debenzylation, yielded trisaccharide 2 in excellent overall yields.…”

Section: Resultsmentioning

confidence: 99%

“…d -Galactosamine thiophenyl glycoside 10 (51) (43.0 mg, 0.044 mmol) and lactose derivative 11 (52) (36.8 mg, 0.066 mmol) were stirred under argon in dry CH 2 Cl 2 (2 mL) for 30 min at rt in the presence of freshly activated, powdered 4A molecular sieves. The reaction mixture was cooled to −70 °C, then treated with N -iodosuccinimide (NIS, 17.8 mg, 0.079 mmol) and a catalytic amount of triflic acid (TfOH, 2.0 mg, 0.0132 mmol).…”

Section: Methodsmentioning

confidence: 99%

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Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens

et al. 2010

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Bishydrazides are versatile linkers for attaching glycans to substrates for lectin binding and pathogen detection schemes. The α,ω-bishydrazides of carboxymethylated hexaethylene glycol (4) can be conjugated at one end to unprotected oligosaccharides, then attached onto carrier proteins, tethered onto activated carboxyl-terminated surfaces, or functionalized with a photoactive crosslinking agent for lithographic patterning. Glycoconjugates of bishydrazide 4 can also be converted into dithiocarbamates (DTCs) by treatment with CS 2 under mild conditions, for attachment onto gold substrates. The immobilized glycans serve as recognition elements for cellsurface lectins and enable the detection and capture of bacterial pathogens such as Psuedomonas aeruginosa by their adsorption onto micropatterned substrates. A detection limit of 10 3 cfu/mL is demonstrated, using a recently introduced method based on optical pattern recognition.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens

et al. 2010

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“…Working towards the completion of the preparation of SLac having polymerizable PEG9 aglycon, our next objective was the synthetic assembly of the SLac moieties by means of radical polymerization. We polymerized various glycomonomers in aqueous media using a convenient radical polymerization technique [ 11 , 24 , 25 ]. Thus, the glycomonomer 9 was allowed to polymerize with or without acryl amide as a mediator for controlling the distance between SLac residues in a 1:1 water—DMSO solvent system in the presence of APS and TEMED as shown in Scheme 3 .…”

Section: Resultsmentioning

confidence: 99%

Use of a Longer Aglycon Moiety Bearing Sialyl α(2→3) Lactoside on the Glycopolymer for Lectin Evaluation

et al. 2023

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A polymerizable alcohol having 9 PEG repeats was prepared in order to mimic an oligosaccharide moiety. Sialyl α(2→3) lactose, which is known as a sugar moiety of GM3 ganglioside, was also prepared, and the polymerizable alcohol was condensed with the sialyl α(2→3) lactose derivative to afford the desired glycomonomer, which was further polymerized with or without acrylamide to give water-soluble glycopolymers. The glycopolymers had higher affinities than those of glycopolymers having sialyl lactose moieties with shorter aglycon moieties.

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“…In nature, the oligosaccharide chains in glycoconjugates play a role and have high specificities in biological events, and a recent report suggested that the affinities of oligosaccharide chains in glycolipids and glycoproteins were enhanced by the self-assembly of glycoconjugates, which display multivalent-type clusters. Much attention has been paid to the formation of synthetic glycoclusters by covalent bonds, and glycodendrimers [ 3 , 4 , 5 ] and glycopolymers [ 6 , 7 , 8 , 9 , 10 ] have been successfully developed. In our ongoing studies of glycopolymers, we have reported a conventional method for the preparation of a glycopolymer by means of Huisgen cycloaddition as a key reaction for the synthesis of monomers and glycopolymers [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis

et al. 2018

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CM-Str (4-(Chloromethyl)styrene) was used as a useful starting material for the construction of a series of functional monomers. Substitution of the chlorine to the corresponding azide was performed, and the reduction of the azide proceeded smoothly to afford an aminostyrene, which was used as a common precursor for the preparation of functional monomers. Condensation of the amine with a fluorophore, biotin and carbohydrate was accomplished. Among the monomers, a carbohydrate monomer was polymerized with or without acrylamide as a model polymerization to yield the corresponding water-soluble glycopolymers, and biological evaluations of the glycopolymers for a lectin, and wheat germ agglutinin (WGA), were carried out on the basis of the fluorescence change of tryptophan in the WGA.

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Practical synthesis of fully protected globotriaose and its glycopolymers

Cited by 17 publications

References 26 publications

Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens

Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens

Use of a Longer Aglycon Moiety Bearing Sialyl α(2→3) Lactoside on the Glycopolymer for Lectin Evaluation

Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis

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