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Laccase mediated-synthesis of hydroxycinnamoyl-peptide from ferulic acid and carnosine

Abstract : Carnosine (CAR) dipeptide was functionalized with ferulic acid(FA) as substrate using laccase from Myceliophtora thermophila asbiocatalyst. The enzymatic reaction was performed in aqueous medium undermild conditions (pH 7.5, 30°C) as an eco-friendly procedure.Results showed that this enzymatic process led to the synthesis of twonew derivatives (P1, P2), from the coupling between CAR and FA derivedproducts. Conditions allowing a high production of P1, P2 derivativeswere determined with an optimal ratio of (FA: CAR) of (1:1.6) at optimaltime reaction of 8 h. Under these optimal conditions, the couplingbetween CAR and FA- products was demonstrated, resulting in the decreaseof -NH2 groups (almost 50%) as quantified via derivatization. Due to thepresence of FA in the structure of these new derivatives, they exhibitedhigher hydrophobic property than carnosine. Structural analyses by massspectrometry showed that P1 and P2 (FA-CAR) derivatives exhibited thesame molecular mass (MM 770 g/mol) containing one CAR-molecule and threeFA-molecules but with different chemical structures. Furthermore, thesederivatives presented improved antioxidant (almost 10 times) and antiproliferative(almost 18 times) properties in comparison with CAR.Moreover, P1 derivative exhibited higher antioxidant and antiproliferativeactivities than P2 derivative, which confirmed thedifferent structures of P1 and P2. These results suggested that theoxidized phenols coupling with carnosine is a promising process toenhance the CAR-properties.
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Abdulhadi Aljawish, Isabelle Chevalot, Nidal Madad, Cédric Paris, Lionel Muniglia. Laccase mediated-synthesis of hydroxycinnamoyl-peptide from ferulic acid and carnosine. Journal of Biotechnology, Elsevier, 2016, p. 1-32. ⟨10.1016/j.jbiotec.2016.04.021⟩. ⟨hal-01687605⟩



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