Chemical ligation via O- to N-acyl transfer of O-acylated serine containing peptides affords serine containing native peptides via 8- and 11-membered cyclic transition states opening the door to a wide variety of potential applications to peptide elaboration. The feasibility of these traceless chemical ligations is feasible as supported by computation.
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http://dx.doi.org/10.1039/c2ob07050b | DOI Listing |
J Org Chem
January 2025
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116, China.
1-Isochromene scaffolds are ubiquitous in natural products and significant bioactive molecules. Although several methods for these molecular syntheses have been developed, reports on the efficient construction of iminated isochromenes are still rather limited. Herein, we report a new Cu(II)-catalyzed annulation and sulfonylimination cascade of α-carbonyl-γ-alkynyl sulfoxonium ylides with sulfamides, enabling direct C-C σ-bond elimination to furnish iminated ()-1-isochromenes in 51-97% yields.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Potsdam 14476, Germany.
Automated glycan assembly (AGA) streamlines the synthesis of complex oligosaccharides. The reducing end of the oligosaccharide serves as an attachment site to the polymer support to liberate a free reducing end or an aminopentanol for ready conjugation to carrier proteins or surfaces. The facile installation of different aglycons on oligosaccharides has not been possible via AGA until now.
View Article and Find Full Text PDFMetabolites
December 2024
Graduate Institute of Biomedical Sciences, China Medical University, Taichung 40402, Taiwan.
J Colloid Interface Sci
March 2025
School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK. Electronic address:
Controllable surface modification of nanoparticulate drug delivery vectors is key to enhancing specific desirable properties such as colloidal stability, targeting, and stimuli-responsive cargo release. Metal-organic frameworks (MOFs) have been proposed as potential delivery devices, with surface modification achieved by various bioconjugate "click" reactions, including copper-catalysed and strain-promoted azide-alkyne cycloaddition. Herein, we show that photo-induced nitrile imine-mediated tetrazole-ene cycloaddition (NITEC) can be used to surface-modify tetrazole-appended Zr MOFs with maleimides, and vice versa, with the extent of this traceless surface functionalisation controlled by the length of photoirradiation.
View Article and Find Full Text PDFNat Commun
November 2024
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
While selective defunctionalizations are valuable in organic synthesis, hydrodeamination of primary amines poses challenges. Deuterodeamination, analogous to hydrodeamination, presents even greater difficulties due to its frequently slower deuteration rate, interference by hydrogenation and constraints in deuterated sources. This study introduces a reliable, robust, and scalable hydro- and deuterodeamination method capable of handling various primary amines.
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