Surfactant-mediated thioglycosylation of 1-hydroxy sugars in water

Ratthachag, Trichada; Buntasana, Supanat; Vilaivan, Tirayut; Padungros, Panuwat

doi:10.1039/d0ob02246b

Cited by 8 publications

(3 citation statements)

References 106 publications

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“…Characterization of the C. glabrata β-glucan structure was then carried out using nuclear magnetic resonance (NMR) spectroscopy (figure 9 and electronic supplementary material, figure S8). NMR characterization of carbohydrates [40][41][42], especially polysaccharides [39,43] can be challenging owing to various factors, such as poor solubility in deuterated solvents [39], the complexity of the carbohydrate structure [44][45][46], and signal overlap between protons of hydroxyl groups and the pyranose/furanose region [40,41]. Initially, C. glabrata β-glucan showed poor solubility in polar deuterated NMR solvents, such as dimethyl sulfoxide (DMSO)-d 6 , D 2 O and CD 3 OD.…”

Section: Morphology and Structural Feature Of C Glabrata β-Glucansmentioning

confidence: 99%

Complement receptor 3-dependent engagement by Candida glabrata β-glucan modulates dendritic cells to induce regulatory T-cell expansion

Kunanopparat,

Dinh,

Ponpakdee

et al. 2024

Open Biol.

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Candida glabrata is an important pathogen causing invasive infection associated with a high mortality rate. One mechanism that causes the failure of Candida eradication is an increase in regulatory T cells (Treg), which play a major role in immune suppression and promoting Candida pathogenicity. To date, how C. glabrata induces a Treg response remains unclear. Dendritic cells (DCs) recognition of fungi provides the fundamental signal determining the fate of the T-cell response. This study investigated the interplay between C. glabrata and DCs and its effect on Treg induction. We found that C. glabrata β-glucan was a major component that interacted with DCs and consequently mediated the Treg response. Blocking the binding of C. glabrata β-glucan to dectin-1 and complement receptor 3 (CR3) showed that CR3 activation in DCs was crucial for the induction of Treg. Furthermore, a ligand–receptor binding assay showed the preferential binding of C. glabrata β-glucan to CR3. Our data suggest that C. glabrata β-glucan potentially mediates the Treg response, probably through CR3-dependent activation in DCs. This study contributes new insights into immune modulation by C. glabrata that may lead to a better design of novel immunotherapeutic strategies for invasive C. glabrata infection.

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Section: Morphology and Structural Feature Of C Glabrata β-Glucansmentioning

confidence: 99%

Complement receptor 3-dependent engagement by Candida glabrata β-glucan modulates dendritic cells to induce regulatory T-cell expansion

Kunanopparat,

Dinh,

Ponpakdee

et al. 2024

Open Biol.

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“…Nevertheless, conducting the chemical reaction in an aqueous solution is a challenge because most organic reactants are water-insoluble and Lewis acid/base catalysts could be deactivated under an aqueous solution. , Nevertheless, some biphasic reaction (on-water reaction) mixtures can be performed, but some of the reactants and products may undergo thermal decomposition when subjected to elevated temperatures in the aqueous reaction mixture, whereas in other instances, water-sensitive reactants exhibit either incompatibility or an inability to react in the presence of water . These obstacles can be mitigated by using micellar systems such as surfactants − or polymeric micelles , of which hydrophobic pockets can encapsulate and stabilize organic substrates in water and thus act as nanoreactors for organic synthesis. Nanoreactor is one of the most promising applications of polymeric micelles. , There are also reports on the use of polymeric micelles as nanocatalysts for organic reactions that can be done under mild conditions .…”

Section: Introductionmentioning

confidence: 99%

Micellar Nanoreactors from Amphiphilic Copolymers for Thia-Michael Addition in Water

Sombat,

Authai,

Padungros

et al. 2023

ACS Appl. Polym. Mater.

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Micellar systems have been recognized as effective nanoreactors for performing chemical reactions in aqueous solutions. This research aims to develop nanoreactors from polymeric micelles in which organic substrates are encapsulated and stabilized within their hydrophobic pockets. An amphiphilic random copolymer, poly(N-(benzyl acrylamide))-ran-poly(N-(2-hydroxypropyl)acrylamide) or PBAM-ran-PHPAM, was first prepared by a simple post-polymerization modification of a polymer precursor, poly(pentafluorophenyl acrylate) (PPFPA), with benzylamine and 1-amino-2-propanol via nucleophilic acyl substitution. The micellar nanoparticles assembled from PBAM-ran-PHPAM were found to be spherical in shape, well-dispersed in water with a diameter of less than 170 nm, and low polydispersity. Thia-Michael addition (or sulfa-Michael addition) between β-nitrostyrenes and thiol derivatives in the presence of the 0.5 wt % PBAM26-ran-PHPAM74 amphiphilic copolymer provide excellent conversions and high isolated yields (75–99%) of the Michael adducts over 20 substrates under ambient conditions. Moreover, the micellar nanoreactors can also be reused up to 10 times while maintaining a respectably high reaction conversion of 75%. This research suggests that the post-polymerization modification of the PPFPA polymer precursor by nucleophilic substitution is a versatile approach to developing customized nanoreactors for diversified chemical reactions in the future.

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“…8 Currently, our research group is aiming to develop surfactant-mediated glycosylations in water using glycosyl chlorides as precursors. 9 Glycosyl chlorides can serve as excellent candidates for glycosylations in micellar systems. Consequently, a reliable and efficient synthesis of glycosyl chlorides is highly desirable.…”

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confidence: 99%

One-Pot Synthesis of Glycosyl Chlorides from Thioglycosides Mediated by a Bromodiethylsulfonium Salt as a Mild Oxidant

Chooppawa

Janprasert

Padungros

2022

Synlett

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Conventional synthesis of glycosyl chlorides from thioglycosides relies on the two sequential oxidation and chlorination. A one-pot synthesis of glycosyl chlorides is warranted as an alternative method. Herein, we report the one-pot synthesis of glycosyl chlorides from thioglycoside precursors. The transformation was mediated at low temperature by bromodiethylsulfonium bromopentachloroantimonate (BDSB) as a mild oxidant and n-Bu4NCl as an additive. The armed thioglycosides afforded the corresponding α-glycosyl chlorides in moderate to good yields under the optimized conditions. Low conversions and yields were obtained when the less reactive disarmed thioglycosides were used. Unexpectedly, BDSB-mediated oxidation of thioglycosides without the addition of n-Bu4NCl also afforded the α-glycosyl chlorides in moderate yields. We suggest a mechanism involving the transfer of chloride ions from the non-nucleophilic bromopentachloroantimonate (SbCl5Br) anion to the oxocarbenium ion.

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Surfactant-mediated thioglycosylation of 1-hydroxy sugars in water

Abstract: Dodecyl benzenesulfonic acid (DBSA)-mediated thioglycosylation in water provided thioglycosides without open-chain dithioacetal sugars, which are common by-products when performing reactions in organic solvent.

Cited by 8 publications

References 106 publications

Complement receptor 3-dependent engagement by Candida glabrata β-glucan modulates dendritic cells to induce regulatory T-cell expansion

Complement receptor 3-dependent engagement by Candida glabrata β-glucan modulates dendritic cells to induce regulatory T-cell expansion

Micellar Nanoreactors from Amphiphilic Copolymers for Thia-Michael Addition in Water

One-Pot Synthesis of Glycosyl Chlorides from Thioglycosides Mediated by a Bromodiethylsulfonium Salt as a Mild Oxidant

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