Enzymatic Resolution of α‐Methyleneparaconic Acids and Evaluation of their Biological Activity |
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| Authors: | Kuheli Chakrabarty Ivana Defrenza Nunzio Denora Sara Drioli Cristina Forzato Massimo Franco Giovanni Lentini Patrizia Nitti Giuliana Pitacco |
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| Affiliation: | 1. Department of Chemistry, Visva‐Bharati, Santiniketan, India;2. Dipartimento di Farmacia – Scienze del Farmaco, Università degli Studi di Bari ‘Aldo Moro’, Bari, Italy;3. Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, Trieste, Italy |
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| Abstract: | Both enantiomers of three biologically relevant paraconic acids—MB‐3, methylenolactocin, and C75—were obtained with enantioselectivities up to 99% by kinetic enzymatic resolutions. Good enantiomeric excesses were obtained for MB‐3 and methylenolactocin, using α‐chymotrypsin and aminoacylase as enantiocomplementary enzymes, while C75 was resolved with aminoacylase. They all were evaluated for their antiproliferative, antibacterial, and antifungal activities, showing weak effects and practically no difference between enantiomers in each case. At high concentrations (16–64 µg/mL), (–)‐ C75 acted as an antimicrobial agent against Gram‐positive bacteria. Chirality 27:239–246, 2015. © 2015 Wiley Periodicals, Inc. |
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| Keywords: | α ‐methylene‐γ ‐butyrolactones MB‐3, methylenolactocin C75 |
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