Experimental and theoretical study of the role of CH/π interactions in the aminolysis reaction of acetyl galactoside

Cuétara‐Guadarrama, Fabián; Hernández-Huerta, Eduardo; Rojo-Portillo, Tania; Reyes-López, Elizabeth; Jiménez‐Barbero, Jesús; Cuevas, Gabriel

doi:10.1016/j.carres.2019.107821

Cited by 6 publications

(3 citation statements)

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“…For example, an aromatic group was used to stabilize the transition state in the aminolysis of acetyl β-galactoside. 104 In an elegant use of CH−π interactions in catalysis, the Jacobsen group carried out rhamnosylations and mannosylations of a broad range of substrates to achieve high β-selectivity. Aromatic residues were appended to a thiourea group that could engage in CH−π interactions in the glycosidic bond-forming transition state (Figure 7).…”

Section: Glycan Reactivitymentioning

confidence: 99%

“…Chemical reactions can also exploit CH−π interactions to enhance reactivity or selectivity. For example, an aromatic group was used to stabilize the transition state in the aminolysis of acetyl β-galactoside . In an elegant use of CH−π interactions in catalysis, the Jacobsen group carried out rhamnosylations and mannosylations of a broad range of substrates to achieve high β-selectivity.…”

Section: Favorable Ch–π Interactions Influence Glycan Reactivitymentioning

confidence: 99%

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CH−π Interactions in Glycan Recognition

Kiessling

Diehl

2021

ACS Chem. Biol.

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Carbohydrate recognition is crucial for biological processes ranging from development to immune system function to host–pathogen interactions. The proteins that bind glycans are faced with a daunting task: to coax these hydrophilic species out of water and into a binding site. Here, we examine the forces underlying glycan recognition by proteins. Our previous bioinformatic study of glycan-binding sites indicated that the most overrepresented side chains are electron-rich aromatic residues, including tyrosine and tryptophan. These findings point to the importance of CH−π interactions for glycan binding. Studies of CH−π interactions show a strong dependence on the presence of an electron-rich π system, and the data indicate binding is enhanced by complementary electronic interactions between the electron-rich aromatic ring and the partial positive charge of the carbohydrate C–H protons. This electronic dependence means that carbohydrate residues with multiple aligned highly polarized C–H bonds, such as β-galactose, form strong CH−π interactions, whereas less polarized residues such as α-mannose do not. This information can guide the design of proteins to recognize sugars and the generation of ligands for proteins, small molecules, or catalysts that bind sugars.

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Section: Glycan Reactivitymentioning

confidence: 99%

Section: Favorable Ch–π Interactions Influence Glycan Reactivitymentioning

confidence: 99%

CH−π Interactions in Glycan Recognition

Kiessling

Diehl

2021

ACS Chem. Biol.

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“…Previous studies have shown that quantum chemistry offers a convenient avenue for studying the structure–activity relationship in bioactive molecules, informing drug development efforts with potential activity motifs. − Consistently, the combination of theoretical and experimental studies can evaluate the antioxidant activity of natural products effectively and accurately. − Thus, in this work, the antioxidant activity of SW from R. harmandiana was investigated by both computational and experimental methods.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Activity of Natural Samwirin A: Theoretical and Experimental Insights

Ngoc

et al. 2021

ACS Omega

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Samwirin A (SW), a natural compound isolated from Sambucus williamsii or Rourea harmandiana, is known to exhibit potent antiosteoporosis activity and promote cell proliferation in rat osteoblast-like UMR 106 cells. Antiosteoporosis activity suggests that the compound must also exhibit antioxidant activity but this has not been studied thus far. In the present study, the antioxidant activity of SW was examined by experimental and computational studies. It was found that SW exhibits good hydroperoxyl scavenging activity, particularly in water at physiological pH (k overall = 1.01 × 107 M–1 s–1). The single-electron transfer mechanism defines the HOO• + SW reaction in water, while the activity in the lipid medium is moderate and it follows the formal hydrogen transfer mechanism. The rate constant of the HOO• scavenging reaction in the aqueous solution is about 78 times higher than the reference compound Trolox. The computational results are in line with experimental data underscoring that SW is a promising radical scavenger in aqueous media at physiological pH.

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Comparative analysis of red and blue-shifting hydrogen bonds in 1:1 haloform complexes

Baburao,

Esakkimuthu,

Ragupathy

2024

Computational and Theoretical Chemistry

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Experimental and theoretical study of the role of CH/π interactions in the aminolysis reaction of acetyl galactoside

Abstract: El artículo seleccionado no se encuentra disponible por ahora a texto completo por no haber sido facilitado todavía por el investigador a cargo del archivo del mismo.

Cited by 6 publications

References 56 publications

CH−π Interactions in Glycan Recognition

CH−π Interactions in Glycan Recognition

Antioxidant Activity of Natural Samwirin A: Theoretical and Experimental Insights

Comparative analysis of red and blue-shifting hydrogen bonds in 1:1 haloform complexes

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