1. High–throughput enantioseparation of Nα–fluorenylmethoxycarbonyl proteinogenic amino acids through fast chiral chromatography on zwitterionic-teicoplanin stationary phases
- Author
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Simone Manetto, Martina Catani, Harald Ritchie, Andrea Orlandin, Walter Cabri, Francesco Gasparrini, Antonio Ricci, Micheal Ye, Claudio Villani, Alberto Cavazzini, Simona Felletti, Giulia Mazzoccanti, Mazzoccanti G, Manetto S, Ricci A, Cabri W, Orlandin A, Catani M, Felletti S, Cavazzini A., Ye M, Ritchie H, Villani C, and Gasparrini F.
- Subjects
chiral synthons ,Nα-FMOC (proteinogenic) amino acids ,superficially-porous CSPs ,zwitterionic-teicoplanin CSPs ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Superficially-porous CSPs ,Analytical Chemistry ,NO ,chemistry.chemical_compound ,Chiral synthons, Superficially-porous CSPs, Nα-FMOC (proteinogenic) amino acids, Zwitterionic-teicoplanin CSPs ,Amino Acids ,Acetonitrile ,Enantiomeric excess ,chemistry.chemical_classification ,Chromatography ,Fluorenes ,Chemistry ,010401 analytical chemistry ,Organic Chemistry ,Synthon ,Enantioselective synthesis ,Proteins ,Stereoisomerism ,General Medicine ,Combinatorial chemistry ,0104 chemical sciences ,Amino acid ,Chiral column chromatography ,Chiral synthons ,Zwitterionic-teicoplanin CSPs ,Teicoplanin ,Enantiomer ,Dispersion (chemistry) ,Porosity ,Chiral synthons Superficially-porous CSPs N α-FMOC (proteinogenic) amino acids Zwitterionic-teicoplanin CSPs - Abstract
In this study, 31 racemates of N α-FMOC (fluorenylmethoxycarbonyl) amino acids (AAs) with different chemico-physical characteristics (neutral nonpolar, neutral polar, acidic and basic) have been success- fully resolved in fast enantioselective chromatography on recently-developed zwitterionic-teicoplanin chi- ral stationary phases (CSPs). The CSPs were prepared by covalently bonding the teicoplanin selector on fully-porous particles of narrow dispersion particle-size distribution (particle diameter 1.9 μm) and superficially-porous particles (2.0 μm). Both the zwitterionic-teicoplanin CSPs have proved to be ideal media for the separation of this important class of compounds. In particular, the zwitterionic CSP pre- pared on superficially-porous particles exhibited superior enantioselectivity and resolution, compared to that made of fully porous particles, in virtue of more favorable thermodynamics. The zwitterionic na- ture of these CSPs allowed avoiding the annoying effect of Donnan’s exclusion of enantiomers from the stationary phase. This effect, on the opposite, was frequently observed on a commercial teicoplanin CSP (Teicoshell) employed for comparative purposes. Noticeably, on the zwitterionic-teicoplanin CSPs, by us- ing either acetonitrile- or methanol-rich mobile phases (MPs), it was possible to favor speed over enan- tioresolution and vice versa. This work gives further replies to the request for rapid determination of enantiomeric excess of N α-FMOC proteinogenic (and non–proteinogenic) AAs, typically used as preferred chiral synthons in the solid-phase synthesis of therapeutic peptides.
- Published
- 2020