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Molecules 2016, 21(1), 25; doi:10.3390/molecules21010025

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

1
Department of Organic Chemistry, ”Iuliu Haţieganu” University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania
2
Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 10 November 2015 / Revised: 17 December 2015 / Accepted: 21 December 2015 / Published: 25 December 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1286 KB, uploaded 25 December 2015]   |  

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. View Full-Text
Keywords: hydrolases; dynamic kinetic resolution; racemisation agent; l-α-amino acids; thiazole hydrolases; dynamic kinetic resolution; racemisation agent; l-α-amino acids; thiazole
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Leonte, D.; Bencze, L.C.; Paizs, C.; Toşa, M.I.; Zaharia, V.; Irimie, F.D. 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 2016, 21, 25.

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