Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines

• Published in: Molecules (Basel, Switzerland) Vol. 21; no. 1; p. E25
• Main Authors: Leonte, Denisa, Bencze, László Csaba, Paizs, Csaba, Toşa, Monica Ioana, Zaharia, Valentin, Irimie, Florin Dan
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 25-12-2015; MDPI
• Subjects: Alanine - chemistry; Amino acids; Antibiotics; Biocatalysis; Carbon; dynamic kinetic resolution; Enzymes; Ethanolamine - chemistry; hydrolases; Kinetics; l-α-amino acids; Lipase - metabolism; Nanotubes, Carbon - chemistry; Peptides; racemisation agent; thiazole; Romania; hydrolases; l-α-amino acids; dynamic kinetic resolution; racemisation agent; thiazole
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules21010025

In this paper we describe the chemoenzymatic synthesis of enantiopure l-2-arylthiazol-4-yl alanines starting from their racemic N-acetyl derivatives; by combining the lipase-catalysed dynamic kinetic resolution of oxazol-5(4H)-ones with a chemical and an enzymatic enantioselective hydrolytic step affording the desired products in good yields (74%-78%) and high enantiopurities (ee > 99%). The developed procedure exploits the utility of the single-walled carbon nanotubes-bound diethylaminoethanol as mild and efficient racemisation agent for the dynamic kinetic resolution of the corresponding oxazolones.