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Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy.
Nat Commun
January 2025
School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China.
Stereocontrolled construction of tetrasubstituted olefins has been an attractive issue yet remains challenging for synthetic chemists. In this manuscript, alkynyl selenides, when treated with ArBCl, are subject to an exclusive 1,1-carboboration, affording tetrasubstituted alkenes with excellent levels of E-selectivity. Detailed mechanistic studies, supported by DFT calculations, elucidates the role of selenium in this 1,1-addition process.
View Article and Find Full Text PDFHighly Selective α-Addition and β-Conjugate Addition Products from Peptides Composed of α,β-Unsaturated γ-Amino Acids.
J Org Chem
January 2025
Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pashan, Pune 411008, India.
β-Addition products are common in conjugate addition reactions consisting of α,β-unsaturated carbonyl compounds. Here, we are reporting an uncommon α-addition product as a major product in the thioacetic acid conjugate addition reaction on a peptide consisting of ()-α,β-unsaturated γ-amino acids. In addition, we observed highly diastereoselective β-addition products from the thiophenol and thioethanol conjugate addition reaction on peptides.
View Article and Find Full Text PDFBorn of frustration: the emergence of Camelina sativa as a platform for lipid biotechnology.
Plant Physiol
January 2025
Rothamsted Research, West Common, Harpenden, Al5 2JQ, UK.
The emerging crop Camelina sativa (L.) Crantz (camelina) is a Brassicaceae oilseed with a rapidly growing reputation for the deployment of advanced lipid biotechnology and metabolic engineering. Camelina is recognised by agronomists for its traits including yield, oil/protein content, drought tolerance, limited input requirements, plasticity and resilience.
View Article and Find Full Text PDFUnveiling Intramolecular [3+2] Cycloaddition Reactions Leading to Functionalized Heterocycles in the Light of Molecular Electron Density Theory.
Chemphyschem
January 2025
Department of Chemistry, Durgapur Government College, West Bengal, Durgapur, 713214, India.
The relative reactivity and cis/trans selectivity of the intramolecular [3+2] cycloaddition (IM32CA) reactions of nitrile oxide (NO), azide (AZ), nitrile sulfide (NS) and nitrile ylide (NY), leading to functionalized heterocycles are studied within the Molecular Electron Density Theory. The kinetically controlled IM32CA reactions are predicted to be cis stereospecific, while the reaction feasibility follows the order NY>NS>NO>AZ with the respective activation Gibbs free energies of 13.7, 17.
View Article and Find Full Text PDFStereospecific Resistance to N2-Acyl Tetrahydro-β-carboline Antimalarials Is Mediated by a PfMDR1 Mutation That Confers Collateral Drug Sensitivity.
ACS Infect Dis
January 2025
Department of Biochemistry and Molecular Biology, University of Georgia, Athens, Georgia 30602, United States.
Half the world's population is at risk of developing a malaria infection, which is caused by parasites of the genus . Currently, resistance has been identified to all clinically available antimalarials, highlighting an urgent need to develop novel compounds and better understand common mechanisms of resistance. We previously identified a novel tetrahydro-β-carboline compound, PRC1590, which potently kills the malaria parasite.
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