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

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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.

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

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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

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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.

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Authors and Affiliations

  1. Department of Chemical Engineering and Materials, Ocean College, Minjiang University, Fuzhou, 350108, Fujian, China

    Lu Huang, Qi Lin, Yanxia Li, Guocai Zheng & Yiting Chen

  2. Singapore University of Technology and Design, 8 Somapah Road, Singapore, Singapore

    Lu Huang

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  1. Lu Huang
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  2. Qi Lin
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Correspondence to Lu Huang or Yiting Chen.

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Huang, L., Lin, Q., Li, Y. et al. Study of the enantioselectivity and recognition mechanism of sulfhydryl-compound-functionalized gold nanochannel membranes. Anal Bioanal Chem 411, 471–478 (2019). https://doi.org/10.1007/s00216-018-1464-1

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  • DOI: https://doi.org/10.1007/s00216-018-1464-1

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