Selective arylation of dichalcogenides in biomolecules

US10117948B2 · kind B2 · utility

Assignee

• Massachusetts Institute of Technology · US

Inventors

• Stephen L. Buchwald · Newton, US
• Bradley L. Pentelute · Cambridge, US
• Daniel Cohen · Watertown, US
• Chi Zhang · Kunshan, CN

Key dates

• Filing date: Jun 20, 2016
• Grant date: Nov 6, 2018
• Expiry date: Jun 20, 2036

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07K14/47
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Disclosed are chemical transformations for the conjugation of unprotected peptide biomolecules. The disclosed chemical transformations relate to methods of selective cysteine and selenocysteine functionalization of unprotected peptide and protein molecules. The processes feature several significant advantages over existing methods of peptide modification, including specificity towards selenocysteine over other nucleophiles (e.g., amines, hydroxyls), excellent functional group tolerance, and mild reaction conditions. Also disclosed are syntheses of arylated cysteine and arylated selenocysteine peptide compounds.