A flavinium catalyst, in conjunction with hydrogen peroxide as stoichiometric oxidant, allowed the aqueous conversion of non-protected thioglycosides into the corresponding glycosyl sulfoxides. These glycosyl sulfoxides displayed only very weak inhibitory activity against corresponding glycosidases.
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http://dx.doi.org/10.1016/j.carres.2015.06.003 | DOI Listing |
Org Biomol Chem
December 2024
Université de Reims Champagne-Ardenne, CNRS, ICMR, Reims, France.
A strategy for the synthesis of 1--substituted thioglycals was developed from cyclic carbohydrate-derived ketene dithioacetals in a four-step sequence. The corresponding thioglycals, in two carbohydrate series, were first obtained by removal of the exocyclic glycosyl sulfoxide, followed by treatment with an organolithium reagent. Various electrophilic groups were introduced onto the thioglycal double bond after deprotonation and formation of a glycosyl lithium intermediate.
View Article and Find Full Text PDFFood Funct
December 2024
Postharvest and Refrigeration Group, Polytechnic University of Cartagena (UPCT), Paseo Alfonso XIII, 48, 30203 Cartagena, Spain.
This study assesses the transformation and stability of polyphenols, sulforaphane, and indoles in a fermented beverage made from broccoli leaves during gastrointestinal digestion (GID). This process was simulated using a dialysis membrane to assess intestinal absorption. The total phenolic compounds (TPC) and antioxidant TEAC assays showed an increase in phytochemical content due to the GID process.
View Article and Find Full Text PDFActa Neurobiol Exp (Wars)
October 2024
Department of Biotechnology, University of Ribeirão Preto, Ribeirão Preto São Paulo, Brazil; Medical School, University of Ribeirão Preto, Ribeirão Preto São Paulo, Brazil.
Chem Commun (Camb)
August 2024
School of Pharmacy, Huazhong University of Science and Technology, Wuhan, Hubei, 430030, China.
Sulfoxides have emerged as pivotal constituents in modern carbohydrate chemistry. As anomeric leaving groups, sulfinyl moieties may occupy positions directly at the anomeric position or at a more remote site. This feature article is focused on the evolution and notable advancements of glycosyl sulfoxide donors in glycosylation reactions.
View Article and Find Full Text PDFOrg Lett
July 2024
School of Pharmacy, Huazhong University of Science and Technology, Wuhan, Hubei 430030, P. R. of China.
We have developed a highly effective glycosylation method that involves the activation of 2-(2-propylsulfinyl)benzyl 1,2-orthoester glycosides using triflic anhydride (TfO). Our research indicates that half of the glycosyl donor is activated through TfO via an interrupted Pummerer reaction mechanism, while the remaining portion is activated by triflic acid (TfOH) generated . As a result, as little as 0.
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