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

Kontrec, Darko; Jurin, Mladenka; Jakas, Andreja; Roje, Marin (2024) New Levan-Based Chiral Stationary Phases: Synthesis and Comparative HPLC Enantioseparation of (±)-trans-β-Lactam Ureas in the Polar Organic Mode. Molecules, 29 (10). ISSN 1420-3049

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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.

Item Type:	Article
Uncontrolled Keywords:	levan; trans-β-lactam ureas; chiral separation; enantioselective HPLC; polar organic mode; polysaccharide-type chiral stationary phases; CSPs; new chiral material
Subjects:	NATURAL SCIENCES > Chemistry NATURAL SCIENCES > Biology > Biochemistry and Molecular Biology
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Bioprospecting Jadranskog mora- Rozelinda Čož-Rakovac; Verica Dragović-Uzelac; Božidar Šantek; Stela Jokić; Igor Jerković; Sandra Kraljević Pavelić KK.01.1.1.01.0002 EK
Depositing User:	Ivana Vuglec
Date Deposited:	17 Oct 2025 09:18
URI:	http://fulir.irb.hr/id/eprint/10005
DOI:	10.3390/molecules29102213

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