1354945-01-9Relevant academic research and scientific papers
Condensation of 2-((Alkylthio)(aryl)methylene)malononitrile with 1,2-Aminothiol as a Novel Bioorthogonal Reaction for Site-Specific Protein Modification and Peptide Cyclization
Gao, Wei,Li, Xuefei,Li, Zhuoru,Luk, Louis Y. P.,Meng, Xiaoting,Tsai, Yu-Hsuan,Wu, Chuanliu,Zhao, Yibing,Zheng, Xiaoli
, (2020)
Site-specific modification of peptides and proteins has wide applications in probing and perturbing biological 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 chemical and physical 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 biological 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.
A dual optical and nuclear imaging reagent for peptide labelling via disulfide bridging
Fletcher, Sally A.,Sin, Pak Kwan Brian,Nobles, Muriel,?rstad, Erik,Tinker, Andrew,Baker, James R.
, p. 9559 - 9563 (2015)
We report a concise approach to a multimodal imaging reagent for peptide labelling via disulfide bridging. The reagent is constructed using a one pot, three component, [3 + 2] cycloaddition of a fluorescent azide with a dithiomaleimide-alkyne, with concom
Synthesis method of thiazoline heterocyclic compound and application of thiazoline heterocyclic compound in biomolecular modification
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Paragraph 0081-0083; 0090-0092, (2020/01/12)
The invention discloses a synthesis method of a thiazoline heterocyclic compound and application of the thiazoline heterocyclic compound in biomolecular modification, and relates to the technical field of organic synthesis. The synthesis method comprises the following steps: mixing a thioalkene ether compound and a compound containing a 1, 2-mercaptoethylamine skeleton structure in a solvent, andadding a weak base to react for 60-240 minutes at the reaction temperature of 20-60 DEG C to obtain the dihydrothiazole heterocyclic compound. The synthesis method of the thiazolidine heterocyclic compound is mild and efficient, can quickly react in water at room temperature, and overcomes the defects of violent reaction conditions, long reaction time and the like in the traditional synthetic method; by means of the synthesis method, biomolecules such as polypeptide and protein containing the nitrogen-terminal cysteine residues can be efficiently and accurately modified, and application of detection and treatment methods and the like is further developed.
