Dynamic Formation of Imidazolidino Boronate Enables Design of Cysteine-Responsive Peptides
| Autor: | Jianmin Gao, Chelsea Weidman, Kaicheng Li |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure 010405 organic chemistry Biomolecule Organic Chemistry Complex formation 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Article 0104 chemical sciences chemistry Biological media Molecule Cysteine Physical and Theoretical Chemistry Peptides |
| Zdroj: | Organic letters. 20(1) |
| ISSN: | 1523-7052 |
| Popis: | We describe the dynamic and chemoselective conjugation between 2-formylphenylboronic acid (2-FPBA) and L-2,3-diaminopropionic acid (L-Dap) yielding an imidazolidino boronate (IzB) complex. The IzB complex formation readily proceeds in biological milieu with little interference by common biomolecules except cysteine. We demonstrate the potential of this reversible conjugation for biological applications by creating “smart” peptides that specifically respond to cysteine in complex biological media. Specifically, the design and characterization of a fluorogenic sensor of cysteine is described. |
| Databáze: | OpenAIRE |
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