Selenoimidazolium Salts as Supramolecular Reagents for Protein Alkylation

Lim, David and Wen, Xiaojin and Seebeck, Florian P.. (2020) Selenoimidazolium Salts as Supramolecular Reagents for Protein Alkylation. Chembiochem : a European journal of chemical biology, 21 (24). pp. 3515-3520.

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Official URL: https://edoc.unibas.ch/81367/

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Se-benzyl selenoimidazolium salts are characterized by remarkable alkyl-transfer potential under physiological conditions. Structure-activity relationship studies show that selective monoalkylation of primary amines depends on supramolecular interactions between the selenoimidazole leaving group and the target nucleophile. We demonstrate that these reagents can be used for site-selective and nearly quantitative modification of the model protein lysozyme on Lys13, bypassing the higher intrinsic reactivities of Lys1 and Lys33. These observations introduce selenoimidazolium salts as novel class of electrophiles for selective N-alkylation of native proteins.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Bionics (Seebeck)
05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann)
UniBasel Contributors:Seebeck, Florian Peter
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:01 Feb 2021 08:48
Deposited On:31 Jan 2021 17:24

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