Elusive dehydroalanine derivatives with enhanced reactivity
Keywords: 
Cycloaddition
Dehydroalanine
Diazo compounds
Methylenoxazolones
Methylidenimidazoleones
Issue Date: 
2019
Publisher: 
Wiley
ISSN: 
1439-4227
Note: 
This article is protected by copyright. All rights reserved
Citation: 
Aydillo-Miguel, C. (Carlos); Mazo, N. (Nuria); Navo, C.D. (Claudio D.); et al. "Elusive dehydroalanine derivatives with enhanced reactivity". ChemBioChem. 20 (10), 2019, 1246 - 1250
Abstract
For the first time, a simple methodology for the chemical synthesis and use of highly reactive 4-methylenoxazol-5(4H)-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.

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