The synthesis of the first examples of a new class of iminosugars based on constrained spirocyclic scaffolds has been achieved via Rh-catalyzed C(sp(3))-H amination. In this process, the needed electronic control in securing high regioselectivity from substrates with a high density of activated C-H bonds was achieved by using a combination of activating and electron-withdrawing groups.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/c5ob01254f | DOI Listing |
Eur J Med Chem
January 2025
Department of Organic Chemistry, Faculty of Chemistry, University of Seville, E-41012, Seville, Spain. Electronic address:
Invariant natural killer T (iNKT) cells are a subset of innate T cells displaying powerful immunomodulatory functions. Despite extensive preclinical research on the use of iNKT agonist and antagonist for various diseases, translating these findings into successful clinical applications has proven challenging, leaving no approved treatments to date. Efforts to optimize therapeutic outcomes by developing alternative glycolipids to α-galactosylceramide (α-GalCer or KRN7000), the prototypical iNKT antigen, have shown improved preclinical results.
View Article and Find Full Text PDFACS Catal
October 2024
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada.
Mutations in many members of the set of human lysosomal glycoside hydrolases cause a wide range of lysosomal storage diseases. As a result, much effort has been directed toward identifying pharmacological chaperones of these lysosomal enzymes. The majority of the candidate chaperones are active site-directed competitive iminosugar inhibitors but these have met with limited success.
View Article and Find Full Text PDFNat Prod Bioprospect
September 2024
Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, 410013, Hunan, China.
Iminosugars, a class of polyhydroxylated cyclic alkaloids with intriguing properties, hold promising therapeutic potentials against a broad spectrum of enveloped viruses, including DENV, HCV, HIV, and influenza viruses. Mechanistically, iminosugars act as the competitive inhibitors of host endoplasmic reticular α-glucosidases I and II to disrupt the proper folding of viral nascent glycoproteins, which thereby exerts antiviral effects. Remarkably, the glycoproteins of many enveloped viruses are significantly more dependent on the calnexin pathway of the protein folding than most host glycoproteins.
View Article and Find Full Text PDFInt J Biol Macromol
October 2024
Division of Bioengineering, Incheon National University, Incheon 22012, Republic of Korea; Research Center for Bio Materials & Process Development, Incheon National University, Incheon 22012, Republic of Korea; Department of Bioengineering and Nano-Bioengineering, Graduate School of Incheon National University, Incheon 22012, Republic of Korea. Electronic address:
The iminosugar class of carbohydrate-active enzyme inhibitors has therapeutic applications in metabolic syndrome conditions, viral infections and cancer. Compared to chemical synthesis, microbial iminosugar production has benefits of cost, sustainability and optimization. In this study, the 1-deoxynojirimycin (DNJ) biosynthetic gene cluster from Bacillus velezensis MBLB0692, and its individual genes, were cloned into Corynebacterium glutamicum (Cg).
View Article and Find Full Text PDFFront Cell Infect Microbiol
August 2024
Department of Bacteriology, Ecology of Microbes and Parasitology, Faculty of Medicine, Jagiellonian University Medical College, Krakow, Poland.
Introduction: Biofilm-associated infections persist as a therapeutic challenge in contemporary medicine. The efficacy of antibiotic therapies is ineffective in numerous instances, necessitating a heightened focus on exploring novel anti-biofilm medical strategies. Among these, iminosugars emerge as a distinctive class of compounds displaying promising biofilm inhibition properties.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!