The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 2,6-dihydroxyhastanecine via reaction sequence involving reduction of the lactone moiety, glycolic cleavage of the terminal diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.carres.2008.04.029 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A two-dimensional fluorescence and chemiluminescence orthogonal probe for discriminating and quantifying similar proteins.
Chem Sci
January 2025
Key Laboratory for Advanced Materials, Institute of Fine Chemicals, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, Center of Photosensitive Chemicals Engineering, East China University of Science and Technology Shanghai 200237 China
Given that proteins with minor variations in amino acid sequences cause distinct functional outcomes, identifying and quantifying similar proteins is crucial, but remains a long-standing challenge. Herein, we present a two-dimensional orthogonal fluorescence and chemiluminescence design strategy for the probe DCM-SA, which is sequentially activated by albumin-mediated hydrolysis, exhibiting light-up fluorescence and photo-induced cycloaddition generating chemiluminescence, enabling orthogonal signal amplification for discrimination of subtle differences between similar proteins. By orthogonalizing these dual-mode signals, a two-dimensional work curve of fluorescence and chemiluminescence is established to distinguish and quantify similar proteins HSA and BSA.
View Article and Find Full Text PDFAluminadichalcogeniranes and Aluminatrichalcogenetanes: Heavier Analogs of Dioxiranes and Trioxetanes.
Angew Chem Int Ed Engl
January 2025
Southern University of Science and Technology, Chemistry, 1088 Xueyuandadao, 518055, Shenzhen, CHINA.
Dioxiranes and their heavier chalcogen analogs have long been recognized as pivotal reagents and intermediates in synthetic chemistry, while trioxetanes have largely remained theoretical constructs. In this work, we present the synthesis of neutral, isoelectronic aluminum/chalcogen analogs of dioxiranes and trioxetanes, specifically aluminadiselenirane, aluminaditellurirane, aluminatriselenetane, aluminatritelluretane, and a mixed Se/Te analog of aluminatrichalcogenetane. These compounds, featuring strained AlCh2 and AlCh3 ring (Ch = Se, Te), exhibit significant polarization between the aluminum and chalcogen components.
View Article and Find Full Text PDFComputational study on novel RhCp (X = CF, SiF, CCl, SOH) as promising catalysts in the [3 + 2] azide-alkyne cycloaddition reaction: insights into mechanistic pathways and reactivity.
Dalton Trans
January 2025
Department of Chemistry, St Berchmans College (Autonomous), Changanassery, Kerala, 686101, India.
This computational study investigated the catalytic efficiency of novel RhCp complexes (X = CF, SiF, CCl, SOH) in [3 + 2] azide-alkyne cycloaddition reactions density functional theory (MN12-L/Def2-SVP). Through quantum mechanical approaches, we explore the impact of different substituents on the Cp* ligand on the mechanism, selectivity, and reactivity of these Rh-based catalysts. Non-covalent interaction (NCI) and reduced density gradient (RDG) analyses, along with frontier molecular orbital (FMO) and Hirshfeld atomic charge analyses, were utilized to assess ligand stability and catalytic performance.
View Article and Find Full Text PDFCu(OTf)-catalyzed multicomponent reactions.
Beilstein J Org Chem
January 2025
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 9, 22100, Como, Italy.
This review reports the achievements in copper(II) triflate-catalyzed processes concerning the multicomponent reactions, applied to the synthesis of acyclic and cyclic compounds. In particular, for the heteropolycyclic systems mechanistic insights were outlined as well as cycloaddition and aza-Diels-Alder reactions were included. These strategies have gained attention due to their highly atom- and step-economy, one-step multi-bond forming, mild reaction conditions, low cost and easy handling.
View Article and Find Full Text PDFSynthesis and Investigation of Peptide-Drug Conjugates Comprising Camptothecin and a Human Protein-Derived Cell-Penetrating Peptide.
Chem Biol Drug Des
January 2025
Research School of Chemistry, Australian National University, Canberra, Australian Capital Territory, Australia.
Drug targeting strategies, such as peptide-drug conjugates (PDCs), have arisen to combat the issue of off-target toxicity that is commonly associated with chemotherapeutic small molecule drugs. Here we investigated the ability of PDCs comprising a human protein-derived cell-penetrating peptide-platelet factor 4-derived internalization peptide (PDIP)-as a targeting strategy to improve the selectivity of camptothecin (CPT), a topoisomerase I inhibitor that suffers from off-target toxicity. The intranuclear target of CPT allowed exploration of PDC design features required for optimal potency.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!