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

Molecules

Denisa Leonte¹  László Csaba Bencze²  Csaba Paizs²  Monica Ioana Toᗺ²  Valentin Zaharia¹  Florin Dan Irimie² 

[1] Department of Organic Chemistry, ”Iuliu Haţieganu” University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania;Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania;

关键词: hydrolases;    dynamic kinetic resolution;    racemisation agent;    l-α-amino acids;    thiazole;   

DOI  :  10.3390/molecules21010025

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.