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

Author(s)

Joao P. F. Vieira ^[1] ; Erick F. Poletti ^[2] ; Renata F. F. Vieira ^[2] ; Vinicius Veredas ^[1] ; Cesar C. Santana ^[3] ; Clovis R. Nakaie ^[2]

Affiliation

^[1] Univ Estadual Campinas Unicamp, Fac Engn Quim, BR-13083852 Campinas, SP - Brazil

^[2] Univ Fed Sao Paulo UNIFESP, EPM, Dept Biofis, BR-04044020 Sao Paulo - Brazil

^[3] Univ Tiradentes UNIT, Nucleo Estudos Sistemas Coloidais Inst Tecnol & P, BR-49032490 Aracaju, SE - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 24, n. 11, p. 1840-1845, 2013-11-00.

Abstract

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. (AU)

• FAPESP's process: 07/56480-0 - Synthesis and studies of peptides and analogues involved principally in the renin-angiotensin and kallikrein-kinin system
• Grantee: clovis ryuichi nakaie
• Support Opportunities: Research Projects - Thematic Grants