Enantiomeric separations of chiral pharmaceuticals using chirally modified tetrahexahedral Au nanoparticles

SURFACE SCIENCE

卷:648

Article

Shukla, N.¹  Yang, D.²  Gellman, A. J.² 

[1] Carnegie Mellon Univ, Inst Complex Engineered Syst, Pittsburgh, PA 15213 USA

[2] Carnegie Mellon Univ, Dept Chem Engn, Pittsburgh, PA 15213 USA

关键词: Propranolol;    Cysteine;    Gold;    Nanoparticles;    Chiral;    Enantioselective;   

DOI  :  10.1016/j.susc.2015.10.061

来源: Elsevier

【 摘 要 】

Tetrahexahedral (THH, 24-sided) Au nanoparticles modified with D- or L-cysteine (Cys) have been used as enantioselective separators of the chiral pharmaceutical propranolol (PLL) in solution phase. Polarimetry has been used to measure the rotation of linearly polarized light by solutions containing mixtures of PLL and Cys/THH-Au NPs with varying enantiomeric excesses of each. Polarimetry yields clear evidence of enantiospecific adsorption of PLL onto the Cys/THH-Au NPs. This extends prior work using propylene oxide as a test chiral probe, by using the crystalline THH Au NPs with well-defined facets to separate a real pharmaceutical. This work suggests that chiral nanoparticles, coupled with a density separation method such as centrifugation, could be used for enantiomeric purification of real pharmaceuticals. A simple robust model developed earlier has also been used to extract the enantiospecific equilibrium constants for R- and S-PLL adsorption onto the D- and L-Cys/THH-Au NPs. (C) 2015 Elsevier B.V. All rights reserved.

【 授权许可】

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