Preparation and Characterization of Branched β-Cyclodextrins Having α-<scp>L</scp>-Fucopyranose and a Study of Their Functions

Nishi, Yuki; Tanimoto, Toshiko

doi:10.1271/bbb.80609

Cited by 11 publications

(5 citation statements)

References 42 publications

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“…[19] and β- l -fucopyranosyl nitromethane ( 16 ) was prepared as described by Phiasivongsa et al . [20] Compounds 20 and 21 were prepared by following the protocols from Nishi and Tanimoto [21] and Daniellou and Narvor [22].…”

Section: Methodsmentioning

confidence: 99%

A Biophysical Study with Carbohydrate Derivatives Explains the Molecular Basis of Monosaccharide Selectivity of the Pseudomonas aeruginosa Lectin LecB

2014

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The rise of resistances against antibiotics in bacteria is a major threat for public health and demands the development of novel antibacterial therapies. Infections with Pseudomonas aeruginosa are a severe problem for hospitalized patients and for patients suffering from cystic fibrosis. These bacteria can form biofilms and thereby increase their resistance towards antibiotics. The bacterial lectin LecB was shown to be necessary for biofilm formation and the inhibition with its carbohydrate ligands resulted in reduced amounts of biofilm. The natural ligands for LecB are glycosides of d-mannose and l-fucose, the latter displaying an unusual strong affinity. Interestingly, although mannosides are much weaker ligands for LecB, they do form an additional hydrogen bond with the protein in the crystal structure. To analyze the individual contributions of the methyl group in fucosides and the hydroxymethyl group in mannosides to the binding, we designed and synthesized derivatives of these saccharides. We report glycomimetic inhibitors that dissect the individual interactions of their saccharide precursors with LecB and give insight into the biophysics of binding by LecB. Furthermore, theoretical calculations supported by experimental thermodynamic data suggest a perturbed hydrogen bonding network for mannose derivatives as molecular basis for the selectivity of LecB for fucosides. Knowledge gained on the mode of interaction of LecB with its ligands at ambient conditions will be useful for future drug design.

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Section: Methodsmentioning

confidence: 99%

A Biophysical Study with Carbohydrate Derivatives Explains the Molecular Basis of Monosaccharide Selectivity of the Pseudomonas aeruginosa Lectin LecB

2014

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“…Regioselective protection of 3 hydroxyl group was achieved using trimethylacetyl chloride 27 in pyridine at 45 °C in good yield to afford 6. Synthesis of the trisaccharide 8 was accomplished by reacting the known β-L-fucopyranosyl trichloroacetimidate 7 29 as donor with acceptor 6 with TMSOTf as promoter in anhydrous diethyl ether and DCM (9:2) solvent in moderate yield and excellent stereo selectivity. The α-isomer of the fucose in the trisaccharides resonated at 5.33 ppm with coupling constant 4.0 Hz in the 1 H NMR and 96.5 ppm in the 13 C NMR.…”

Section: ■ Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Biotinylated Bivalent HistoBlood Group Antigens for Capturing Human Noroviruses

et al. 2016

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A panel of biotinylated bivalent H-type glycans that have been reported as binding ligands for human noroviruses were synthesized using a modular synthetic strategy. These glycoconjugates were attached to streptavidin-coated magnetic beads and used to recover human norovirus from fecal samples using a magnetic bead-based assay. The biotinylated bivalent glycans synthesized for this study exhibited similar or better capturing ability when compared to commercial biotinylated glycopolymers.

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“…Optical rotations were measured on a Jasco P‐2000 polarimeter. Compounds 13 , 15 , 16 , 17 , 30 , 31 , 32 b , 33 , and 37 were previously reported and prepared by using literature methods. For the synthesis and characterization of key intermedates 18 , 20 , 21 , 23 – 26 , 34 – 36 , 38 – 49 , see the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

trans‐Stilbene C‐Glycosides: Synthesis by a Microwave‐Assisted Heck Reaction and Evaluation of the SGLT‐2 Inhibitory Activity

et al. 2017

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Ap rotocol for the microwave-assisted Heck coupling reaction of C-aryl glycosides and styrenes has been developed for the synthesis of mono-and bis(C-glycoside) stilbenes. This method exclusively provides C-glycoside transstilbenes in good yields. The Pd-catalyzed Heck coupling reaction was successfully appliedt ov arious functionalized Cglycosyl aryl iodides and variouss ubstituted styrenes to deliver several C-glycoside trans-stilbenes with high selectivity. The obtained C-glycosyl trans-stilbenes were also examined for human SGLT-2i nhibitory activity.

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Preparation and Characterization of Branched β-Cyclodextrins Having α-L-Fucopyranose and a Study of Their Functions

Cited by 11 publications

References 42 publications

A Biophysical Study with Carbohydrate Derivatives Explains the Molecular Basis of Monosaccharide Selectivity of the Pseudomonas aeruginosa Lectin LecB

A Biophysical Study with Carbohydrate Derivatives Explains the Molecular Basis of Monosaccharide Selectivity of the Pseudomonas aeruginosa Lectin LecB

Synthesis and Evaluation of Biotinylated Bivalent HistoBlood Group Antigens for Capturing Human Noroviruses

trans‐Stilbene C‐Glycosides: Synthesis by a Microwave‐Assisted Heck Reaction and Evaluation of the SGLT‐2 Inhibitory Activity

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