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Elusive Dehydroalanine Derivatives with Enhanced Reactivity |
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| Authors: | Dr Carlos Aydillo Nuria Mazo Dr Claudio D Navo Dr Gonzalo Jiménez-Osés |
| Affiliation: | 1. Departamento de Química, Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain
Department of Pharmaceutical Technology and Chemistry, Faculty of Pharmacy and Nutrition, University of Navarra, Irunlarrea 3, 31008 Pamplona, Spain Instituto de Investigación Sanitaria de Navarra (IdiSNA), Irunlarrea 3, 31008 Pamplona, Spain These authors contributed equally to this work.;2. Departamento de Química, Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain These authors contributed equally to this work.;3. Departamento de Química, Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain CIC bioGUNE, Bizkaia Technology Park, Building 801A, 48170 Derio, Spain These authors contributed equally to this work.;4. Departamento de Química, Universidad de La Rioja, Madre de Dios, 53, 26006 Logroño, Spain |
| 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. |
| Keywords: | cycloaddition dehydroalanine diazo compounds methylenoxazolones methylidenimidazoleones |