The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations. [reaction--see text]
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol049483s | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
On the Role of Hydrogen Migrations in the Taxadiene System.
Angew Chem Int Ed Engl
January 2025
Kekulé Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany.
Taxa-4,11-diene is made by the taxa-4,11-diene synthase (TxS) from Taxus brevifolia. The unique reactivity of the taxane system is characterised by long distance hydrogen migrations in the biosynthesis. This study demonstrates that selective long range hydrogen migrations also play a role in the high energy process of the EI-MS fragmentation of taxa-4,11-diene.
View Article and Find Full Text PDFSame, but different: Variations in fragment ions among stereoisomers of a 17α-methyl steroid in gas chromatography/electron ionization mass spectrometry.
Rapid Commun Mass Spectrom
January 2025
Institute of Pharmacy, Berlin, Germany.
Rationale: Gas chromatography/electron ionization mass spectrometry (GC/EI-MS) is a well-established tool for the identification of unknown compounds such as new metabolites of xenobiotics. But it reaches the limits of confident structural assignment if it comes to stereoisomers. This work helps to overcome this difficulty by getting a deeper comprehension of composition of so far unspecific and also characteristic fragment ions in general and comparison among stereoisomers.
View Article and Find Full Text PDFStructure and functional studies of Avt1, a novel peptide from the sea anemone Aulactinia veratra.
Biochim Biophys Acta Proteins Proteom
January 2025
Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC 3052, Australia; ARC Centre for Fragment-Based Design, Monash University, Parkville, VIC 3052, Australia. Electronic address:
Sea anemones are a rich source of peptide toxins spanning a diverse range of biological activities, typically targeting proteins such as ion channels, receptors and transporters. These peptide toxins and their analogues are usually highly stable and selective for their molecular targets, rendering them of interest as molecular tools, insecticides and therapeutics. Recent transcriptomic and proteomic analyses of the sea anemone Aulactinia veratra identified a novel 28-residue peptide, designated Avt1.
View Article and Find Full Text PDFThe Myosin-V Myo51 and Alpha-Actinin Ain1p Cooperate during Contractile Ring Assembly and Disassembly in Fission Yeast Cytokinesis.
J Fungi (Basel)
September 2024
Molecular Biomedical Sciences Department, College of Veterinary Medicine, North Carolina State University, Raleigh, NC 27607, USA.
Cytokinesis is driven in part by the constriction of a ring of actin filaments, myosin motors and other proteins. In fission yeast, three myosins contribute to cytokinesis including a Myosin-V Myo51. As Myosin-Vs typically carry cargo along actin filaments, the role of Myo51 in cytokinesis remains unclear.
View Article and Find Full Text PDFStructural insights into ternary immunocomplex formation and cross-reactivity: binding of an anti-immunocomplex FabB12 to Fab220-testosterone complex.
FEBS J
November 2024
Department of Chemistry, University of Eastern Finland, Joensuu, Finland.
Anti-immunocomplex (Anti-IC) antibodies have been used in developing noncompetitive immunoassays for detecting small molecule analytics (haptens). These antibodies bind specifically to the primary antibody in complex with hapten. Although several anti-IC antibody-based immunoassays have been developed, structural studies of these systems are very limited.
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!