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Assembly of Pyrenes through a Quadruple Photochemical Cascade: Blocking Groups Allow Diversion from the Double Mallory Path to Photocyclization at the Bay Region.
J Am Chem Soc
December 2024
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.
We present a six-step cascade that converts 1,3-distyrylbenzenes (-stilbenes) into nonsymmetric pyrenes in 40-60% yields. This sequence merges photochemical steps, ,-alkene isomerization, a 6π photochemical electrocyclization (Mallory photocyclization); the new bay region cyclization, with two radical iodine-mediated aromatization steps; and an optional aryl migration. This work illustrates how the inherent challenges of engineering excited state reactivity can be addressed by logical design.
View Article and Find Full Text PDFRadical Alkylcyanation of 1,6-Enynes with Isonitriles as Bifunctional Reagents.
Org Lett
December 2024
State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai 201620, China.
We report a radical cyano-cyclization of 1,6-enynes with isonitriles via photochemically driven nickel catalysis, forging alkenyl nitrile-tethered γ-lactams under mild conditions. This reaction leverages the photoexcitation of generated nickel (isonitrile) species to facilitate isonitriles serving as alkyl radical precursors and cyanide sources. The reaction accommodates a wide range of substrates, exhibiting excellent regioselectivity and / stereoselectivity.
View Article and Find Full Text PDFMechanistic Investigation of a Photoredox Cycloaddition Chain Reaction.
J Am Chem Soc
December 2024
Department of Chemistry, Binghamton University, Binghamton, New York 13902, United States.
Photoredox catalysis is important in modern organic chemistry and the development of new synthetic methods. Mechanistic insights, particularly with photoredox chain reactions, are underdeveloped. This study combines quantum yield (QY) measurements, transient absorption spectroscopy (TAS), and electrochemical analysis to rigorously characterize the mechanism and rate constants of a ruthenium-catalyzed photoredox chain [4 + 2] cyclization between -anethole and isoprene.
View Article and Find Full Text PDFSynthesis of Bis-Thioacid Derivatives of Diarylethene and Their Photochromic Properties.
ACS Omega
December 2024
Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia 23529, United States.
Diarylethenes (DAEs) are an important class of photoswitchable compounds that typically undergo reversible photochemical conversions between the open and closed cyclized forms upon treatment with UV light or visible light. In this study, we introduced thioacid functional groups to several photochromic dithienylethene (DTE) derivatives and established a method that can be used to prepare these photoswitchable thioacids. Four thioacid-functionalized diarylethene derivatives were synthesized through the activation of carboxylic acids with -hydroxysuccinimide, followed by reactions with sodium hydrosulfide with yields over 90%.
View Article and Find Full Text PDFSequencing the monoclonal antibody variable regions using multiple charge integration middle-down strategy and ultraviolet photodissociation.
Anal Chim Acta
January 2025
CAS Key Laboratory of Separation Sciences for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China; State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China; University of Chinese Academy of Sciences, Beijing, 100049, China. Electronic address:
Article Synopsis
- Therapeutic monoclonal antibodies (mAbs) are important in targeted therapies due to their specificity and low side effects, making their CDR sequencing essential.
- A new mass spectrometry strategy (MCI-MDMS) using ultraviolet photodissociation (UVPD) allows for greater sequence coverage of mAbs, achieving over 95% with complete CDR coverage.
- This method not only improves sequencing accuracy but also enables reliable identification of post-translational modifications, providing a valuable tool for developing therapeutic mAbs and related biopharmaceuticals.
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