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Chirality. 2013 Nov;25(11):751-6. doi: 10.1002/chir.22208. Epub 2013 Jul 11.

Preparative separation of enantiomers based on functional nucleic acids modified gold nanoparticles.

Author information

1
Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety (Fuzhou University), and Department of Chemistry, Fuzhou University, Fuzhou, Fujian, China.

Abstract

The preparative-scale separation of chiral compounds is vitally important for the pharmaceutical industry and related fields. Herein we report a simple approach for rapid preparative separation of enantiomers using functional nucleic acids modified gold nanoparticles (AuNPs). The separation of DL-tryptophan (DL-Trp) is demonstrated as an example to show the feasibility of the approach. AuNPs modified with enantioselective aptamers were added into a racemic mixture of DL -Trp. The aptamer-specific enantiomer (L-Trp) binds to the AuNPs surface through aptamer-L-Trp interaction. The separation of DL-Trp is then simply accomplished by centrifugation: the precipitate containing L-Trp bounded AuNPs is separated from the solution, while the D-Trp remains in the supernatant. The precipitate is then redispersed in water. The aptamer is denatured under 95 °C and a second centrifugation is then performed, resulting in the separation of AuNPs and L-Trp. The supernatant is finally collected to obtain pure L-Trp in water. The results show that the racemic mixture of DL-Trp is completely separated into D-Trp and L-Trp, respectively, after 5 rounds of repeated addition of fresh aptamer-modified AuNPs to the DL-Trp mixture solution. Additionally, the aptamer-modified AuNPs can be repeatedly used for at least eight times without significant loss of its binding ability because the aptamer can be easily denatured and renatured in relatively mild conditions. The proposed approach could be scaled up and extended to the separation of other enantiomers by the adoption of other enantioselective aptamers.

KEYWORDS:

DL-tryptophan; aptamer; chiral compounds; gold nanoparticles; preparative-scale enantioseparation

PMID:
23846867
DOI:
10.1002/chir.22208
[Indexed for MEDLINE]
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