Published April 1, 2019
| Version v1
Journal article
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Elusive Dehydroalanine Derivatives with Enhanced Reactivity
- 1. Department of Pharmaceutical Technology and Chemistry Faculty of Pharmacy and Nutrition, University of Navarra. Instituto de Investigacijn Sanitaria de Navarra (IdiSNA). Departamento de Qu&mica, Universidad de La Rioja.
- 2. Departamento de Química, Universidad de La Rioja.
- 3. CIC bioGUNE. Departamento de Química, Universidad de La Rioja.
Description
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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