Alternative and simple normal-phase HPLC enantioseparation of a chiral amino acid-type spin label derivative

Journal of the Brazilian Chemical Society

Joao P. F. Vieira²  Erick F. Poletti¹  Renata F. F. Vieira¹  Vinicius Veredas²  Cesar C. Santana¹  Clovis R. Nakaie¹ 

[1] ,Universidade Estadual de Campinas Faculdade de Engenharia Química Campinas SP ,Brazil

关键词: spin label;    peptide;    column chromatography;    chiral compound;   

DOI  :  10.5935/0103-5053.20130229

来源: SciELO

【 摘 要 】

In this work an alternative chromatographic process was developed for fractionating the (+)-(3R,4R) and ( - )-(3S,4S) enantiomers of the chiral trans β-amino acid trans-2,2,5,5-tetramethylpyrrolidine-3-amino-4-carboxylic acid (POAC), which was protected at its amine group for further coupling to a peptide, polymer or other macromolecule. The HPLC enantioseparation was achieved using a chiral cellulose-based normal stationary phase and isocratic elution. The n-hexane:isopropanol system, always with greater amount of the former component, was used as mobile phase as revealed by improved fractionation property of both components, demonstrated by the separation factor and resolution index values. These parameters presented values of 3.7 and 18.4 and of 2.0 and 6.7 when in 90:10 (v/v) and 80:20 (v/v) n-hexane:isopropanol solutions, respectively. These findings indicate that the one-step chromatographic purification strategy using normal-phase is feasible, thus opening the perspective of a fast large-scale production this paramagnetic spin probe.

【 授权许可】

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