Food‐Related Carbohydrate Ligands for Galectins

Mossine, Valeri V.; Glinsky, Vladislav V.; Mawhinney, Thomas P.

doi:10.1002/9780470378076.ch12

Cited by 4 publications

(10 citation statements)

References 88 publications

(105 reference statements)

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“…1 H and 13 C nuclear magnetic resonance (NMR) spectra were recorded at 25°C at 500 and 125.7 MHz, respectively, using a Bruker Avance II 500 spectrometer. For 1 H, 13 C nuclear magnetic resonance (NMR) spectra, chemical shifts are reported in parts per million relative to tetramethylsilane or a residual solvent peak (CHCl 3 : 1 H: δ 7.26 ppm, 13 C: δ 77.2 ppm). Assignments of 1 H and 13 C were assisted by 2D 1 H-COSY and 2D 1 H- 13 C experiments.…”

Section: General Methodsmentioning

confidence: 99%

“…For 1 H, 13 C nuclear magnetic resonance (NMR) spectra, chemical shifts are reported in parts per million relative to tetramethylsilane or a residual solvent peak (CHCl 3 : 1 H: δ 7.26 ppm, 13 C: δ 77.2 ppm). Assignments of 1 H and 13 C were assisted by 2D 1 H-COSY and 2D 1 H- 13 C experiments. In the description of the spectra, the signals corresponding to the glucose or trehalose moieties were labeled as "G" or "T", respectively.…”

Section: General Methodsmentioning

confidence: 99%

“…affinity. For example, the affinity of lactitol for several human galectins drops substantially compared to that of lactose [13,14]. The higher flexibility of the sorbitol moiety should also impact on the hydration of this residue, an a higher interaction with the solvent would account for the lower affinity [15].…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

“…The protected products were O-deacetylated by treatment with triethylamine in aqueous methanol, then desalted with an exchange resin and finally purified by reverse-phase chromatography to give the fully unprotected monovalent (12) and divalent ligands (15, 18 and 22). In parallel series of reactions, the succinyl diamide monovalent (13) and divalent (16, 20 and 24) analogues were obtained. Compounds 13 and 16 had been previously reported and were synthesized again for the purpose of this study [33], whereas compounds 20 and 24 were obtained by click coupling of 9 and 6 (→19) or 10 and 6 (→23) and subsequent deacetylation.…”

Section: Synthesismentioning

confidence: 99%

“…Compound (2,3,4,6-tetr (17) Compound 17 was obtained by reaction of 5 and 9. Column solvent system: CHCl 3 13…”

Section: 2′33′44′-hexa-o-acetyl-66'-dideoxy-66'-bis-{4-[23-dmentioning

confidence: 99%

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Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process

Cano

Varela

García‐Moreno

et al. 2017

Carbohydrate Research

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The synthesis of mono and divalent β-galactosylamides linked to a hydroxylated chain having a C2 symmetry axis derived from l-tartaric anhydride is reported. Reference compounds devoid of hydroxyl groups in the linker were also prepared from β-galactosylamine and succinic anhydride. After functionalization with an alkynyl residue, the resulting building blocks were grafted onto different azide-equipped scaffolds through the copper catalyzed azide-alkyne cycloaddition. Thus, a family of structurally related mono and divalent β-N-galactopyranosylamides was obtained and fully characterized. The binding affinities of the ligands towards the model lectin PNA were measured by the enzyme-linked lectin assay (ELLA). The IC values were significantly higher than that of galactose but the presence of hydroxyl groups in the aglycone chain improved lectin recognition. Docking and molecular dynamics experiments were in accordance with the hypothesis that a hydroxyl group properly disposed in the linker could mimic the Glc O3 in the recognition process. On the other hand, divalent presentation of the ligands led to lectin affinity enhancements.

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Section: General Methodsmentioning

confidence: 99%

Section: General Methodsmentioning

confidence: 99%

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

“…Compound (2,3,4,6-tetr (17) Compound 17 was obtained by reaction of 5 and 9. Column solvent system: CHCl 3 13…”

Section: 2′33′44′-hexa-o-acetyl-66'-dideoxy-66'-bis-{4-[23-dmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process

Cano

Varela

García‐Moreno

et al. 2017

Carbohydrate Research

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Chemical Synthesis of Oligosaccharides Related to the Cell Walls of Plants and Algae

et al. 2017

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Plant cell walls are composed of an intricate network of polysaccharides and proteins that varies during the developmental stages of the cell. This makes it very challenging to address the functions of individual wall components in cells, especially for highly complex glycans. Fortunately, structurally defined oligosaccharides can be used as models for the glycans, to study processes such as cell wall biosynthesis, polysaccharide deposition, protein-carbohydrate interactions, and cell-cell adhesion. Synthetic chemists have focused on preparing such model compounds, as they can be produced in good quantities and with high purity. This Review contains an overview of those plant and algal polysaccharides that have been elucidated to date. The majority of the content is devoted to detailed summaries of the chemical syntheses of oligosaccharide fragments of cellulose, hemicellulose, pectin, and arabinogalactans, as well as glycans unique to algae. Representative synthetic routes within each class are discussed in detail, and the progress in carbohydrate chemistry over recent decades is highlighted.

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Crystal structure and hydrogen bonding inN-(1-deoxy-β-D-fructopyranos-1-yl)-2-aminoisobutyric acid

2018

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Food‐Related Carbohydrate Ligands for Galectins

Cited by 4 publications

References 88 publications

Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process

Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process

Chemical Synthesis of Oligosaccharides Related to the Cell Walls of Plants and Algae

Crystal structure and hydrogen bonding inN-(1-deoxy-β-D-fructopyranos-1-yl)-2-aminoisobutyric acid

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