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General and Facile Route to Isomerically Pure Tricyclic Peptides Based on Templated Tandem CLIPS/CuAAC Cyclizations 下载免费PDF全文
Gaston J. J. Richelle Sumeet Ori Prof. Dr. Henk Hiemstra Prof. Dr. Jan H. van Maarseveen Prof. Dr. Peter Timmerman 《Angewandte Chemie (International ed. in English)》2018,57(2):501-505
We report a one‐pot ligation/cyclization technology for the rapid and clean conversion of linear peptides into tricyclic peptides that is based on using tetravalent scaffolds containing two benzyl bromide and two alkyne moieties. These react via CLIPS/CuAAC reactions with cysteines and azides in the peptide. Flexibility in the scaffolds is key to the formation of isomerically pure products as the flexible scaffolds T4 1 and T4 2 mostly promote the formation of single isomeric tricycles while the rigid scaffolds T4 3 and T4 4 do not yield clean products. There seems to be no limitation to the number and types of amino acids present as 18 canonical amino acids were successfully implemented. We also observed that azides at the peptide termini and cysteine residues in the center gave better results than compounds with the functional groups placed the other way round. 相似文献
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Cheng Fan WarrenE. Piers Masood Parvez 《Angewandte Chemie (International ed. in English)》2009,48(16):2808-2808
Perfluoroaryl boranes are an important class of organometallic Lewis acids. The synthesis of perfluorinated compounds brings special challenges to tried‐and‐true synthetic methodologies. In their Communication on page 2955 ff., W. E. Piers and co‐workers present the synthesis of a new, fully fluorinated heterocyclic borane that is also a member of the rare antiaromatic borole class of compounds. The route relies on normally facile transmetallation reactions made more difficult by the electron‐withdrawing C6F5 groups of the target product.
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Srijanani Bhaskar Jonathon Hitt Sei‐Won Laura Chang Joerg Lahann Prof. 《Angewandte Chemie (International ed. in English)》2009,48(25):4452-4452
Multicompartmental microcylinders can be produced by a combination of electrohydrodynamic co‐spinning and microsectioning, as described by J. Lahann et al. in their Communication on page 4589 ff. The number of individual compartments, relative compartment orientation, chemical composition and functionality, and aspect ratio can be precisely tuned. Each color in the longitudinal and cross‐sectional micrograph images depicts an individual compartment.
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