Stereoselective Oxidative Bioconjugation of Amino Acids and Oligopeptides to Aldehydes

Autor:	Henriette N. Tobiesen, Karl Anker Jørgensen, Lars A. Leth, Marc V. Iversen, Line Næsborg, Søren Bertelsen
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Bioconjugation chemistry Carboxylic acid Organocatalysis Oxidative coupling of methane General Medicine Bioorthogonal chemistry Combinatorial chemistry Quinone Stereocenter Amino acid
Zdroj:	Angewandte Chemie. 132:18648-18652
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202008513
Popis:	The first stereoselective, near-equimolar, and metal-free oxidative bioconjugation of amino acids and oligopeptides to aldehydes is presented. Based on a newly developed organocatalytic oxidative concept, the C-terminal and side-chain carboxylic acid functionalities of amino acids and oligopeptides are shown to couple in a stereoselective manner to α-branched aldehydes catalyzed by a chiral primary amine and a quinone as oxidizing agent. The oxidative coupling generally proceeds in high yield. For aspartic acid, selective coupling of the side-chain, or the C-terminal carboxylic acid, is demonstrated depending on the protection strategy. The stereoselective, oxidative bioconjugation concept is extended to a series of oligopeptides where coupling to carboxylic acid functionalities is presented. Bioorthogonal linker molecules for further functionalization are obtained by merging the oxidative coupling strategy with the click concept. It is demonstrated that the configuration of the new stereocenter is determined exclusively by the organocatalyst.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fcc55d975cac85f18cdd87152ec64d4d https://doi.org/10.1002/ange.202008513 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.