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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Synthesis and Applications of the Se-N Clickable and Orthogonal Linker Based on Bicyclo[1.1.1]pentane
Yinglu Wang1, Weijie Zheng1, Youkun Liu1
1Fujian-Taiwan Science and Technology Cooperation Base of Biomedical Materials and Tissue Engineering, Engineering Research Center of Industrial Biocatalysis, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350117, China.
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Despite the metabolic and geometric advantages of bicyclo[1.1.1]pentane (BCP), click-ready orthogonal BCP linkers remain limited. We report an azide-selenoxide bifunctional BCP linker via azido selenenylation of [1.1.1]propellane and oxidation, installing a benzyl selenoxide and an azide at opposite termini. The selenoxide enables benzyne trapping and interrupted Pummerer functionalization of phenols, including tyrosine-selective modification of oligopeptides, while the azide supports CuAAC, Staudinger ligation, and reductive acylation.
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