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Enantioselective permeations of amino acids through l-proline-modified gold nanochannel membrane: an experimental and theoretical study

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Abstract

l-Proline-modified gold nanochannel membrane (l-Pro-GNM) was prepared and applied for the enantioselective permeations of amino acid enantiomers including tyrosine (Tyr), tryptophan (Trp) and phenylalanine (Phe). Experimental results show that l-Pro-GNM has enantioselectivities for Tyr and Phe enantiomers. Furthermore, the chiral recognition mechanism was studied by density functional theory (DFT) and reduced density gradient (RDG). DFT computational results illustrate that the fundamental chiral recognition system contains two chiral selectors and one selectand, which can be used to evaluate the enantioselective efficiencies of other chiral compounds and the enantioselective ability of other potential amino acid-modified GNM. Finally, graphs obtained by RDG using Multiwfn show helpful visual interactions between the chiral selector and selectand. Results indicate that the electrostatic interaction and hydrogen bonding are responsible for the binding of the chiral selector and selectand, and the larger binding energy shows larger van der Waals interactions.

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Abbreviations

AA:

Amino acid

CS:

Chiral selector

DFT:

Density functional theory

GNM:

Gold nanochannel membrane

l-Pro:

l-Proline

l-Pro-GNM:

l-Pro modified gold nanochannel membrane

PBS:

Phosphate buffer solution

PCM:

Polycarbonate membrane

Phe:

Phenylalanine

RDG:

Reduced density gradient

RSD:

Relative standard deviation

SA:

Selectand

SEM:

Scanning electron microscope

SMD:

Solvation model density

Trp:

Tryptophan

Tyr:

Tyrosine

XPS:

X-ray photoelectron spectroscopy

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Acknowledgements

We acknowledge the financial support by the National Nature Sciences Funding of China (21405075), Natural Sciences Funding of Fujian Province (2017J01418, 2016J05040), Fujian Provincial Youth Natural Fund Key Project (JZ160468) and Science and technology project of Minjiang University (MYK17008, MYK17010). We also acknowledge the use of High-Performance Computing (HPC) service of National Supercomputing Centre (Singapore) in carrying out this work.

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Authors and Affiliations

  1. Department of chemical engineering and materials, Ocean College, Minjiang University, Fuzhou, 350108, People’s Republic of China

    Lu Huang, Yanxia Li, Qi Lin, Benyong Lou & 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. Yanxia Li
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The manuscript was written through contributions of all authors and they have given approval to the final version of the manuscript.

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Correspondence to Yiting Chen.

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This article does not contain any studies with human participants or animals performed by any of the authors. This article does not contain studies with human or animal subjects performed by any of the authors that should be approved by Ethics Committee.

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Huang, L., Li, Y., Lin, Q. et al. Enantioselective permeations of amino acids through l-proline-modified gold nanochannel membrane: an experimental and theoretical study. Amino Acids 50, 1549–1556 (2018). https://doi.org/10.1007/s00726-018-2629-0

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