Cargando…

Helical springs as a color indicator for determining chirality and enantiomeric excess

Chirality plays a key role in the physiological system, because molecular functionalities may drastically alter due to a change in chirality. We report herein a unique color indicator with a static helicity memory, which exhibits visible color changes in response to the chirality of chiral amines. A...

Descripción completa

Detalles Bibliográficos
Autores principales: Maeda, Katsuhiro, Hirose, Daisuke, Nozaki, Mai, Shimizu, Yoichi, Mori, Taro, Yamanaka, Kentaro, Ogino, Koji, Nishimura, Tatsuya, Taniguchi, Tsuyoshi, Moro, Munetsugu, Yashima, Eiji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Association for the Advancement of Science 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8245042/
https://www.ncbi.nlm.nih.gov/pubmed/34193429
http://dx.doi.org/10.1126/sciadv.abg5381
_version_ 1783716039979171840
author Maeda, Katsuhiro
Hirose, Daisuke
Nozaki, Mai
Shimizu, Yoichi
Mori, Taro
Yamanaka, Kentaro
Ogino, Koji
Nishimura, Tatsuya
Taniguchi, Tsuyoshi
Moro, Munetsugu
Yashima, Eiji
author_facet Maeda, Katsuhiro
Hirose, Daisuke
Nozaki, Mai
Shimizu, Yoichi
Mori, Taro
Yamanaka, Kentaro
Ogino, Koji
Nishimura, Tatsuya
Taniguchi, Tsuyoshi
Moro, Munetsugu
Yashima, Eiji
author_sort Maeda, Katsuhiro
collection PubMed
description Chirality plays a key role in the physiological system, because molecular functionalities may drastically alter due to a change in chirality. We report herein a unique color indicator with a static helicity memory, which exhibits visible color changes in response to the chirality of chiral amines. A difference of less than 2% in the enantiomeric excess (ee) values causes a change in the absorption that is visible to the naked eyes. This was further quantified by digital photography by converting to RGB values. This system relies on the change in the tunable helical pitch of the π-conjugated polymer backbone in specific solvents and allows rapid on-site monitoring of chirality of nonracemic amines, including drugs, and the simultaneous quantitative determination of their ee values.
format Online
Article
Text
id pubmed-8245042
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Association for the Advancement of Science
record_format MEDLINE/PubMed
spelling pubmed-82450422021-07-13 Helical springs as a color indicator for determining chirality and enantiomeric excess Maeda, Katsuhiro Hirose, Daisuke Nozaki, Mai Shimizu, Yoichi Mori, Taro Yamanaka, Kentaro Ogino, Koji Nishimura, Tatsuya Taniguchi, Tsuyoshi Moro, Munetsugu Yashima, Eiji Sci Adv Research Articles Chirality plays a key role in the physiological system, because molecular functionalities may drastically alter due to a change in chirality. We report herein a unique color indicator with a static helicity memory, which exhibits visible color changes in response to the chirality of chiral amines. A difference of less than 2% in the enantiomeric excess (ee) values causes a change in the absorption that is visible to the naked eyes. This was further quantified by digital photography by converting to RGB values. This system relies on the change in the tunable helical pitch of the π-conjugated polymer backbone in specific solvents and allows rapid on-site monitoring of chirality of nonracemic amines, including drugs, and the simultaneous quantitative determination of their ee values. American Association for the Advancement of Science 2021-06-30 /pmc/articles/PMC8245042/ /pubmed/34193429 http://dx.doi.org/10.1126/sciadv.abg5381 Text en Copyright © 2021 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution License 4.0 (CC BY). https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution license (https://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Maeda, Katsuhiro
Hirose, Daisuke
Nozaki, Mai
Shimizu, Yoichi
Mori, Taro
Yamanaka, Kentaro
Ogino, Koji
Nishimura, Tatsuya
Taniguchi, Tsuyoshi
Moro, Munetsugu
Yashima, Eiji
Helical springs as a color indicator for determining chirality and enantiomeric excess
title Helical springs as a color indicator for determining chirality and enantiomeric excess
title_full Helical springs as a color indicator for determining chirality and enantiomeric excess
title_fullStr Helical springs as a color indicator for determining chirality and enantiomeric excess
title_full_unstemmed Helical springs as a color indicator for determining chirality and enantiomeric excess
title_short Helical springs as a color indicator for determining chirality and enantiomeric excess
title_sort helical springs as a color indicator for determining chirality and enantiomeric excess
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8245042/
https://www.ncbi.nlm.nih.gov/pubmed/34193429
http://dx.doi.org/10.1126/sciadv.abg5381
work_keys_str_mv AT maedakatsuhiro helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT hirosedaisuke helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT nozakimai helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT shimizuyoichi helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT moritaro helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT yamanakakentaro helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT oginokoji helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT nishimuratatsuya helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT taniguchitsuyoshi helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT moromunetsugu helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess
AT yashimaeiji helicalspringsasacolorindicatorfordeterminingchiralityandenantiomericexcess