New Levan-Based Chiral Stationary Phases: Synthesis and Comparative HPLC Enantioseparation of (±)-trans-β-Lactam Ureas in the Polar Organic Mode

Author:

Kontrec Darko1,Jurin Mladenka1ORCID,Jakas Andreja1ORCID,Roje Marin1ORCID

Affiliation:

1. Laboratory for Chiral Technologies, Division of Organic Chemistry and Biochemistry, Ruder Bošković Institute, Bijenička Cesta 54, 10 000 Zagreb, Croatia

Abstract

In this paper, the preparation of three new polysaccharide-type chiral stationary phases (CSPs) based on levan carbamates (3,5-dimethylphenyl, 4-methylphenyl, and 1-naphthyl) is described. The enantioseparation of (±)-trans-β-lactam ureas 1a–h was investigated by high-performance liquid chromatography (HPLC) on six different chiral columns (Chiralpak AD-3, Chiralcel OD-3, Chirallica PST-7, Chirallica PST-8, Chirallica PST-9, and Chirallica PST-10) in the polar organic mode, using pure methanol (MeOH), ethanol (EtOH), and acetonitrile (ACN). Apart from the Chirallica PST-9 column (based on levan tris(1-naphthylcarbamate), the columns exhibited a satisfactory chiral recognition ability for the tested trans-β-lactam ureas 1a–h.

Funder

European Regional Development Fund-the Competitiveness and Cohesion Operational Pro-gramme

project Bioprospecting of the Adriatic Sea

Publisher

MDPI AG

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