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

Denisa Leonte; László Csaba Bencze; Csaba Paizs; Monica Ioana Toşa; Valentin Zaharia; Florin Dan Irimie

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

Molecules. 2015 Dec 25;21(1):E25. doi: 10.3390/molecules21010025.

Authors

Denisa Leonte¹, László Csaba Bencze², Csaba Paizs³, Monica Ioana Toşa⁴, Valentin Zaharia⁵, Florin Dan Irimie⁶

Affiliations

¹ Department of Organic Chemistry, "Iuliu Haţieganu" University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania. hapau.denisa@umfcluj.ro.
² Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. cslbencze@chem.ubbcluj.ro.
³ Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. paizs@chem.ubbcluj.ro.
⁴ Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. mtosa@chem.ubbcluj.ro.
⁵ Department of Organic Chemistry, "Iuliu Haţieganu" University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania. vzaharia@umfcluj.ro.
⁶ Biocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. irimie@chem.ubbcluj.ro.

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.

Keywords: dynamic kinetic resolution; hydrolases; l-α-amino acids; racemisation agent; thiazole.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alanine / chemistry
Biocatalysis
Ethanolamine / chemistry*
Kinetics
Lipase / metabolism*
Nanotubes, Carbon / chemistry*

Substances

Nanotubes, Carbon
Ethanolamine
Lipase
Alanine