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

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Article in Molecules (Basel, Switzerland), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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6 authors.

Denisa LeonteDepartment of Organic Chemistry, "Iuliu Haţieganu" University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania. hapau.denisa@umfcluj.ro.

László Csaba BenczeBiocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. cslbencze@chem.ubbcluj.ro.

Csaba PaizsBiocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. paizs@chem.ubbcluj.ro.

Monica Ioana ToşaBiocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. mtosa@chem.ubbcluj.ro.

Valentin ZahariaDepartment of Organic Chemistry, "Iuliu Haţieganu" University of Medicine and Pharmacy, RO-400012 Cluj-Napoca, Victor Babeş 41, Romania. vzaharia@umfcluj.ro.

Florin Dan IrimieBiocatalysis and Biotransformation Research Group, Babeş-Bolyai University, RO-400028 Cluj-Napoca, Arany János 11, Romania. irimie@chem.ubbcluj.ro.

Funding

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6 · The paper itself

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.

Indexed as

AlanineBiocatalysisEthanolamineKineticsLipaseNanotubes, CarbonAlanineEthanolamineLipaseNanotubes, Carbondynamic kinetic resolutionhydrolasesl-α-amino acidsracemisation agentthiazole

Identifiers

PMID26712727

DOI10.3390/molecules21010025

PMCPMC6273000

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