Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution |
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| Authors: | Paola D’Arrigo Lorenzo Cerioli Andrea Fiorati Stefano Servi Fiorenza Viani Davide Tessaro |
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| Institution: | 1. Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘Giulio Natta’, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133 Milano, Italy;2. Centro Interuniversitario di Ricerca in Biotecnologie Proteiche ‘The Protein Factory’, Politecnico di Milano, Università degli studi dell’Insubria and ICRM, CNR Milano, Via Mancinelli 7, 20131 Milano, Italy;3. ICRM, CNR Via Mancinelli 7, 20131 Milano, Italy |
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| Abstract: | A double catalyst system (protease + base) was applied to the dynamic kinetic resolution (DKR) of isomeric 1- and 2-α-naphthyl-glycines and -alanines exploiting the in situ racemization of their thioesters. Due to the different C-acidity of the two sets of compounds, different experimental conditions have been devised to perform the simultaneous resolution/racemization process.In all cases, the racemic N-Boc-thioesters were converted into the aminoacids with an l-configuration almost quantitatively and with complete enantioselectivity. |
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