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Analytical and Bioanalytical Chemistry

, Volume 411, Issue 2, pp 471–478 | Cite as

Study of the enantioselectivity and recognition mechanism of sulfhydryl-compound-functionalized gold nanochannel membranes

  • Lu HuangEmail author
  • Qi Lin
  • Yanxia Li
  • Guocai Zheng
  • Yiting ChenEmail author
Research Paper
  • 44 Downloads

Abstract

Two new chiral membranes were prepared by modification of gold nanochannel membranes with d-penicillamine and N-acetyl-l-cysteine and were characterized by scanning electron microscopy and X-ray photoelectron spectroscopy. The effects of key factors such as the gold deposition time, the pH, and the concentration of sodium dihydrogen phosphate on the separation factor are discussed. Chiral resolution of amino acid enantiomers by the chiral membranes was investigated. The experimental results show that the d-penicillamine-modified membrane has good enantioselectivity toward tyrosine and phenylalanine enantiomers, whereas the N-acetyl-l-cysteine-modified membrane has good enantioselectivity toward tyrosine and tryptophan enantiomers. Furthermore, the chiral recognition mechanism was studied by density functional theory. The calculation results indicate that the basic chiral recognition system of d-penicillamine complexes involves only one chiral selector and one selected enantiomer, whereas that of N-acetyl-l-cysteine complexes involves two chiral selectors and one selected enantiomer. Finally, the NH3+ group of d-penicillamine is proved to play an important role in enhancing interactions between complexes and improving enantioselectivity.

Graphical abstract

Enantioselective interactions between amino acid enantiomers and sulfhydryl-compound-functionalized gold nanochannel membranes

Keywords

Chiral resolution Chiral nanochannel membrane Sulfhydryl compounds Recognition mechanism Density functional theory 

Abbreviations

AA

Amino acid

CS

Chiral selector

DFT

Density functional theory

d-PA

d-Penicillamine

GNM

Gold nanochannel membrane

NALC

N-Acetyl-l-cysteine

PBS

Phosphate buffer solution

PCM

Polycarbonate membrane

Phe

Phenylalanine

SE

Selected enantiomer

Trp

Tryptophan

Tyr

Tyrosine

Notes

Acknowledgements

This work was supported by the Natural Sciences Funding of Fujian Province (2017J01418, 2016J05040), the Fujian Provincial Youth Natural Fund Key Project (JZ160468), and the Science and Technology Project of Minjiang University (MYK17008, MYK17010). The authors thank the National Supercomputing Centre (Singapore) for the use of the high-performance computing service.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

Supplementary material

216_2018_1464_MOESM1_ESM.pdf (143 kb)
ESM 1 (PDF 142 kb)

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemical Engineering and Materials, Ocean CollegeMinjiang UniversityFuzhouChina
  2. 2.Singapore University of Technology and DesignSingaporeSingapore

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