Elusive Dehydroalanine Derivatives with Enhanced Reactivity. (1st April 2019)

• Record Type: Journal Article
• Authors: Aydillo, Carlos; Mazo, Nuria; Navo, Claudio D.; Jiménez‐Osés, Gonzalo
• Is Part Of: Chembiochem. Volume 20:Number 10(2019)
• Page Start: 1246
• Page End: 1250
• Publication Date: 2019-04-01
• Subjects: cycloaddition -- dehydroalanine -- diazo compounds -- methylenoxazolones -- methylidenimidazoleones; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.201800758
• Languages: English
• ISSNs: 1439-4227

Abstract

Abstract: For the first time, a simple methodology for the chemical synthesis and use of highly reactive 4‐methylenoxazol‐5(4 H )‐ones from serine is presented. These dehydroalanine derivatives, which resemble the natural 4‐methylidenimidazole‐5‐one (MIO) cofactor present in lyases and aminomutases, undergo rapid reaction with carbon nucleophiles such as silyl enol ethers, as well as cycloaddition reactions with diazo compounds and reactive dienes, under very mild conditions and without any need for metal catalysts or ring‐strain activation, offering potential for bioconjugation. Abstract : Site‐selective bioconjugation and post‐translational modification of proteins under physiological conditions : A highly reactive and elusive dehydroalanine scaffold has been prepared for the first time. It reacted quickly in situ with a variety of reagents without any need for extra activation, thus paving the way for bioconjugation applications.