title: 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.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, "Iuliu Haţieganu" University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania. hapau.denisa@umfcluj.ro.
authors.forename: Denisa
authors.initials: D
authors.lastname: Leonte
authors.affiliation: Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. cslbencze@chem.ubbcluj.ro.
authors.forename: László Csaba
authors.initials: LC
authors.lastname: Bencze
authors.affiliation: Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. paizs@chem.ubbcluj.ro.
authors.forename: Csaba
authors.initials: C
authors.lastname: Paizs
authors.affiliation: Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. mtosa@chem.ubbcluj.ro.
authors.forename: Monica Ioana
authors.initials: MI
authors.lastname: Toşa
authors.affiliation: Department of Organic Chemistry, "Iuliu Haţieganu" University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania. vzaharia@umfcluj.ro.
authors.forename: Valentin
authors.initials: V
authors.lastname: Zaharia
authors.affiliation: Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. irimie@chem.ubbcluj.ro.
authors.forename: Florin Dan
authors.initials: FD
authors.lastname: Irimie
mesh_terms: D000409:Alanine / Q000737:chemistry; D055162:Biocatalysis; D019856:Ethanolamine / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D037742:Nanotubes, Carbon / Q000737:chemistry*
chemical_list: D037742:Nanotubes, Carbon; D019856:Ethanolamine; D008049:Lipase; D000409:Alanine
keywords: dynamic kinetic resolution; hydrolases; l-α-amino acids; racemisation agent; thiazole