On March 18, 2020, Zheng, Xiaoli; Li, Zhuoru; Gao, Wei; Meng, Xiaoting; Li, Xuefei; Luk, Louis Y. P.; Zhao, Yibing; Tsai, Yu-Hsuan; Wu, Chuanliu published an article.COA of Formula: C10H14O3 The title of the article was Condensation of 2-((Alkylthio)(aryl)methylene)malononitrile with 1,2-Aminothiol as a Novel Bioorthogonal Reaction for Site-Specific Protein Modification and Peptide Cyclization. And the article contained the following:
Site-specific modification of peptides and proteins has wide applications in probing and perturbing biol. systems. Herein we report that 1,2-aminothiol can react rapidly, specifically and efficiently with 2-((alkylthio)(aryl)methylene)malononitrile (TAMM) under biocompatible conditions. This reaction undergoes a unique mechanism involving thiol-vinyl sulfide exchange, cyclization, and elimination of dicyanomethanide to form 2-aryl-4,5-dihydrothiazole (ADT) as a stable product. An 1,2-aminothiol functionality can be introduced into a peptide or a protein as an N-terminal cysteine or an unnatural amino acid. The bioorthogonality of this reaction was demonstrated by site-specific labeling of not only synthetic peptides and a purified recombinant protein but also proteins on mammalian cells and phages. Unlike other reagents in bioorthogonal reactions, the chem. and phys. properties of TAMM can be easily tuned. TAMM can also be applied to generate phage-based ADT-cyclic peptide libraries without reducing phage infectivity. Using this approach, we identified ADT-cyclic peptides with high affinity to different protein targets, providing valuable tools for biol. studies and potential therapeutics. Furthermore, the mild reaction conditions of TAMM condensation warrant its use with other bioorthogonal reactions to simultaneously achieve multiple site-specific modifications. The experimental process involved the reaction of (Trimethoxymethyl)benzene(cas: 707-07-3).COA of Formula: C10H14O3
The Article related to sequence alkylthio aryl methylene malononitrile aminothiol bioorthogonal reaction, bioorthogonal reaction protein modification peptide cyclization, Biochemical Methods: Reagents and other aspects.COA of Formula: C10H14O3
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