Enantioselective Liquid–Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde

Qian Chen; Yingji Jin; Haofei Huang; Zhishan Su; Seong Kyu Kim; Kwan Mook Kim

doi:10.1002/bkcs.11533

Enantioselective Liquid–Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde

Qian Chen, Yingji Jin, Haofei Huang, Zhishan Su, Seong Kyu Kim, Kwan Mook Kim

Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The derivative of aminophenyl-aldehyde with an asymmetric carbon and an uryl group, (S)-2, was synthesized. The combination of (S)-2 and aliquat-336 in CDCl₃ extracted underivatized amino acids in water layer by imine formation with enantioselectivities of 12/1 for Phe, 13/1 for Val, and 12/1 for Leu, which are comparable with those of previously reported binaphthol-based extractor (S)-1. The enantioselectivities of (S)-2 is remarkable considering the low molecular weight compared to (S)-1. Density functional theory computations and experimental data demonstrate that imine bond is strengthened by resonance-assisted hydrogen bond with the nearby NH group.

Original language	English
Pages (from-to)	960-964
Number of pages	5
Journal	Bulletin of the Korean Chemical Society
Volume	39
Issue number	8
DOIs	https://doi.org/10.1002/bkcs.11533
State	Published - Aug 2018

Bibliographical note

Funding Information:
Acknowledgments. This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017 R1A2B2009672).

Publisher Copyright:
© 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Amino acid
Chiral extractor
Liquid–liquid extraction

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10.1002/bkcs.11533

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title = "Enantioselective Liquid–Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde",

abstract = "The derivative of aminophenyl-aldehyde with an asymmetric carbon and an uryl group, (S)-2, was synthesized. The combination of (S)-2 and aliquat-336 in CDCl3 extracted underivatized amino acids in water layer by imine formation with enantioselectivities of 12/1 for Phe, 13/1 for Val, and 12/1 for Leu, which are comparable with those of previously reported binaphthol-based extractor (S)-1. The enantioselectivities of (S)-2 is remarkable considering the low molecular weight compared to (S)-1. Density functional theory computations and experimental data demonstrate that imine bond is strengthened by resonance-assisted hydrogen bond with the nearby NH group.",

keywords = "Amino acid, Chiral extractor, Liquid–liquid extraction",

author = "Qian Chen and Yingji Jin and Haofei Huang and Zhishan Su and Kim, {Seong Kyu} and Kim, {Kwan Mook}",

note = "Funding Information: Acknowledgments. This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017 R1A2B2009672). Publisher Copyright: {\textcopyright} 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Chen, Qian

AU - Jin, Yingji

AU - Huang, Haofei

AU - Su, Zhishan

AU - Kim, Seong Kyu

AU - Kim, Kwan Mook

N1 - Funding Information: Acknowledgments. This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017 R1A2B2009672). Publisher Copyright: © 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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Y1 - 2018/8

N2 - The derivative of aminophenyl-aldehyde with an asymmetric carbon and an uryl group, (S)-2, was synthesized. The combination of (S)-2 and aliquat-336 in CDCl3 extracted underivatized amino acids in water layer by imine formation with enantioselectivities of 12/1 for Phe, 13/1 for Val, and 12/1 for Leu, which are comparable with those of previously reported binaphthol-based extractor (S)-1. The enantioselectivities of (S)-2 is remarkable considering the low molecular weight compared to (S)-1. Density functional theory computations and experimental data demonstrate that imine bond is strengthened by resonance-assisted hydrogen bond with the nearby NH group.

AB - The derivative of aminophenyl-aldehyde with an asymmetric carbon and an uryl group, (S)-2, was synthesized. The combination of (S)-2 and aliquat-336 in CDCl3 extracted underivatized amino acids in water layer by imine formation with enantioselectivities of 12/1 for Phe, 13/1 for Val, and 12/1 for Leu, which are comparable with those of previously reported binaphthol-based extractor (S)-1. The enantioselectivities of (S)-2 is remarkable considering the low molecular weight compared to (S)-1. Density functional theory computations and experimental data demonstrate that imine bond is strengthened by resonance-assisted hydrogen bond with the nearby NH group.

KW - Amino acid

KW - Chiral extractor

KW - Liquid–liquid extraction

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SN - 0253-2964

VL - 39

SP - 960

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JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 8

ER -

Enantioselective Liquid–Liquid Extraction of Underivatized Amino Acids with Simple Chiral Aminophenyl-Aldehyde

Abstract

Bibliographical note

Keywords

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