Synthesis of alkyne-tagged and biotin-tagged Sortin1 as novel photoaffinity probes
| Autor: | Kaori Sakurai, Rina Komatsu, Yoshihiro Ozeki, Tamayo Yamaguchi, Naohiro Kobayashi |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Pyridines
Stereochemistry Clinical Biochemistry Biotin Pharmaceutical Science Alkyne Photoaffinity Labels Conjugated system 010402 general chemistry 01 natural sciences Biochemistry DNA-binding protein Structure-Activity Relationship chemistry.chemical_compound Drug Discovery Benzophenone Moiety Molecular Biology chemistry.chemical_classification Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Binding protein Organic Chemistry 0104 chemical sciences Indenes chemistry Alkynes Molecular Medicine Biogenesis |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 28:1562-1565 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2018.03.060 |
| Popis: | Sortin1 is an inhibitor of vesicular biogenesis and transport, which is shared among eukaryotes and plants with an unknown mode of action. Toward exploration of its target proteins, we developed alkyne as well as biotin conjugated photoaffinity probes derived from Sortin1. Due to the presence of phenylketone moiety, Sortin1 was anticipated to serve as a photoreactive group in a similar manner to a commonly used photoreactive group, benzophenone. The core structure based on 5-oxo-1,4-dihydroindenopyridine was constructed in one step using three-component Hantzsch dihydropyridine synthesis. We demonstrated that Sortin1 displayed photocrosslinking reactivity against a model binding protein, which would be useful for capturing and detecting binding proteins. |
| Databáze: | OpenAIRE |
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