Enantioselective separation of (±)‐β‐hydroxy‐1,2,3‐triazoles by supercritical fluid chromatography and high‐performance liquid chromatography

• Published in: Chirality (New York, N.Y.) Vol. 30; no. 7; pp. 890 - 899
• Main Authors: Alvarenga, Natália, Porto, André L.M., Barreiro, Juliana Cristina
• Format: Journal Article
• Language: English
• Published: United States Wiley Subscription Services, Inc 01-07-2018
• Subjects: Amylose; biocatalysis; Biological properties; Cellulose; Chromatography; enantiomeric separation; Enantiomers; Ethanol; Fungi; High performance liquid chromatography; HPLC; Liquid chromatography; Optimization; Penicillium citrinum; Polysaccharides; Propanol; Separation; SFC; Stationary phase; Supercritical fluids; Triazoles; triazoles; SFC; enantiomeric separation; HPLC; biocatalysis
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.22851

This paper reports the enantioseparation of β‐hydroxy‐1,2,3‐triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high‐performance liquid chromatography techniques (HPLC). Polysaccharide‐based chiral columns (cellulose and amylose) were used to evaluate the separation in SFC and HPLC. Time of analyses, consumption of solvent, and parameter optimization were reduced using SFC technique. The columns based on cellulose chiral stationary phase using 2‐propanol and ethanol as modifiers showed the best results for the enantioresolution of the (±)‐β‐hydroxy‐1,2,3‐triazoles by SFC analyses. These techniques were applied to evaluate the selectivity of biocatalytic reduction of β‐keto‐1,2,3‐triazoles by marine‐derived fungus Penicillium citrinum CBMAI 1186 to obtain the (±)‐β‐hydroxy‐1,2,3‐triazoles.
Enantioseparation of (±)‐β‐hydroxy‐1,2,3‐triazole derivatives by supercritical fluid chromatography and high‐performance liquid chromatography techniques.