Discrimination of the Chirality of α-Amino Acids in ZnII Complexes of DPA-Appended Binaphthyl Imine

Mukesh Eknath Shirbhate; Raju Nandhakumar; Youngmee Kim; Sung Jin Kim; Seong Kyu Kim; Kwan Mook Kim

doi:10.1002/ejoc.201800321

Discrimination of the Chirality of α-Amino Acids in Zn^II Complexes of DPA-Appended Binaphthyl Imine

Mukesh Eknath Shirbhate, Raju Nandhakumar, Youngmee Kim, Sung Jin Kim, Seong Kyu Kim, Kwan Mook Kim

Chemistry & Nanoscience

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

4 Scopus citations

Abstract

Binaphthol aldehydes with appended dipicolylamine moieties, (R)-1, and (R)-2, were synthesized. The reaction of (R)-1 with an amino acid together with the Zn^II ion produces a monomeric complex that discriminates the chirality of the bound amino acid by ¹H NMR spectroscopy. The same reaction of (R)-2, which is different from (R)-1 by only one nitrogen atom, generates a dimeric complex that is highly enantiospecific for the l-form of amino acids such as Phe and Trp.

Original language	English
Pages (from-to)	4959-4964
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	35
DOIs	https://doi.org/10.1002/ejoc.201800321
State	Published - 23 Sep 2018

Bibliographical note

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

Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Amino acids
Chirality
Enantioselectivity
Zinc

Access to Document

10.1002/ejoc.201800321

Cite this

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title = "Discrimination of the Chirality of α-Amino Acids in ZnII Complexes of DPA-Appended Binaphthyl Imine",

abstract = "Binaphthol aldehydes with appended dipicolylamine moieties, (R)-1, and (R)-2, were synthesized. The reaction of (R)-1 with an amino acid together with the ZnII ion produces a monomeric complex that discriminates the chirality of the bound amino acid by 1H NMR spectroscopy. The same reaction of (R)-2, which is different from (R)-1 by only one nitrogen atom, generates a dimeric complex that is highly enantiospecific for the l-form of amino acids such as Phe and Trp.",

keywords = "Amino acids, Chirality, Enantioselectivity, Zinc",

author = "Shirbhate, {Mukesh Eknath} and Raju Nandhakumar and Youngmee Kim and Kim, {Sung Jin} and Kim, {Seong Kyu} and Kim, {Kwan Mook}",

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

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T1 - Discrimination of the Chirality of α-Amino Acids in ZnII Complexes of DPA-Appended Binaphthyl Imine

AU - Shirbhate, Mukesh Eknath

AU - Nandhakumar, Raju

AU - Kim, Youngmee

AU - Kim, Sung Jin

AU - Kim, Seong Kyu

AU - Kim, Kwan Mook

N1 - Funding Information: This work was supported by a National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (no. NRF-2017R1A2B2009672). Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/9/23

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N2 - Binaphthol aldehydes with appended dipicolylamine moieties, (R)-1, and (R)-2, were synthesized. The reaction of (R)-1 with an amino acid together with the ZnII ion produces a monomeric complex that discriminates the chirality of the bound amino acid by 1H NMR spectroscopy. The same reaction of (R)-2, which is different from (R)-1 by only one nitrogen atom, generates a dimeric complex that is highly enantiospecific for the l-form of amino acids such as Phe and Trp.

AB - Binaphthol aldehydes with appended dipicolylamine moieties, (R)-1, and (R)-2, were synthesized. The reaction of (R)-1 with an amino acid together with the ZnII ion produces a monomeric complex that discriminates the chirality of the bound amino acid by 1H NMR spectroscopy. The same reaction of (R)-2, which is different from (R)-1 by only one nitrogen atom, generates a dimeric complex that is highly enantiospecific for the l-form of amino acids such as Phe and Trp.

KW - Amino acids

KW - Chirality

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KW - Zinc

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