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A straightforward synthesis of carbohydrate templated isoxazolidines is described, by reaction of unprotected glycosylhydroxylamines (operating as 1,3-dipoles) with methyl acrylate using microwave activation. Rhamno- and erythro-isoxazolidines are recognized by plant cells, resulting in a strong ROS-production as a plant immune response, and exert a high antifungal activity against Botrytis cinerea.
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http://dx.doi.org/10.1016/j.bioorg.2023.106829 | DOI Listing |
Chem Pharm Bull (Tokyo)
September 2025
Peptide Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan.
Conventional peptide synthesis involves multiple protection and deprotection steps, and typically relies on stoichiometric amounts of coupling reagents and additives. This makes the process cumbersome, and results in poor atom economy and hazardous waste generation. Therefore, direct peptide bond formation using unprotected amino acids is a promising alternative.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India.
The guaianolides represent an array of complex sesquiterpene natural products with the basic 5-7-5-ring structure. An efficient diastereoselective allylation of a functionalized aldehyde with an allyl bromolactone, translactonization and aldehyde-ene reactions paved an excellent path toward the protecting-group-free divergent total synthesis of (-)-integrifolin, (+)-8--grosheimin and (+)-grosheimin. The common intermediate molecule ligustrin was synthesized and further extended through various compatible reactions to more complex guaianolides.
View Article and Find Full Text PDFBioconjug Chem
July 2025
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
The synthesis of neoglycoconjugates has paved the way for the discovery of novel probes that mimic natural glycoconjugates and can provide designed research tools and therapeutics. In some cases, the target protein may not be amenable to harsh conditions; therefore, semisynthetic or chemical methods must be chosen with care. Here, we present a simple and modular chemoselective coupling strategy between an unprotected sugar and an ,-disubstituted hydroxylamine under mild acidic conditions.
View Article and Find Full Text PDFRSC Chem Biol
July 2025
Department of Chemistry, City University of Hong Kong Tat Chee Avenue, Kowloon Hong Kong P. R. China
Photoactivatable systems have received considerable attention in the development of diagnostics and therapeutics due to their noninvasive nature and precise spatiotemporal control. Of particular interest is the 3,6-dithio-1,2,4,5-tetrazine (,-tetrazine) unit, which can not only act as a photolabile protecting group for constructing photoactivatable systems but also as a bioorthogonal scaffold that enables the inverse electron-demand Diels-Alder (IEDDA) cycloaddition reaction with strained alkynes. In this study, we designed and synthesised a cyclometallated iridium(iii) complex modified with a 3-chloro-6-thio-1,2,4,5-tetrazine moiety (1) for cysteine conjugation.
View Article and Find Full Text PDFChemistry
July 2025
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
The synthesis of p-nitrophenol-β-C-glycosides from native mono-, di-, and trisaccharides is described. The one-pot-two-step procedure uses water as the solvent and produces exclusively β-C-glycosides, the desired stereochemistry for most medicinal chemistry applications. The versatility of the approach is illustrated by the synthesis of the nanomolar SGLT2 inhibitor [3-(4-ethylbenzyl)phenyl]-β-C-glucoside.
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