Cargando…

Identifying a Hidden Conglomerate Chiral Pool in the CSD

[Image: see text] Conglomerate crystallization is the spontaneous generation of individually enantioenriched crystals from a nonenantioenriched material. This behavior is responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The phenomenon of conglomerate crysta...

Descripción completa

Detalles Bibliográficos
Autores principales: Walsh, Mark P., Barclay, James A., Begg, Callum S., Xuan, Jinyi, Johnson, Natalie T., Cole, Jason C., Kitching, Matthew O.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9597607/
https://www.ncbi.nlm.nih.gov/pubmed/36311827
http://dx.doi.org/10.1021/jacsau.2c00394
_version_ 1784816131954966528
author Walsh, Mark P.
Barclay, James A.
Begg, Callum S.
Xuan, Jinyi
Johnson, Natalie T.
Cole, Jason C.
Kitching, Matthew O.
author_facet Walsh, Mark P.
Barclay, James A.
Begg, Callum S.
Xuan, Jinyi
Johnson, Natalie T.
Cole, Jason C.
Kitching, Matthew O.
author_sort Walsh, Mark P.
collection PubMed
description [Image: see text] Conglomerate crystallization is the spontaneous generation of individually enantioenriched crystals from a nonenantioenriched material. This behavior is responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The phenomenon of conglomerate crystallization of chiral organic molecules has been left largely undocumented, with no actively curated list available in the literature. While other crystallographic behaviors can be interrogated by automated searching, conglomerate crystallizations are not identified within the Cambridge Structural Database (CSD) and are therefore not accessible by conventional automated searching. By conducting a manual search of the CSD and literature, a list of over 1800 chiral species capable of conglomerate crystallization was curated by inspection of the racemic synthetic routes described in each publication. The majority of chiral conglomerate crystals are produced and published by synthetic chemists who seldom note and rarely exploit the implications this phenomenon can have on the enantiopurity of their crystalline materials. With their structures revealed, we propose that this list of compounds represents a new chiral pool which is not tied to biological sources of chirality.
format Online
Article
Text
id pubmed-9597607
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-95976072022-10-27 Identifying a Hidden Conglomerate Chiral Pool in the CSD Walsh, Mark P. Barclay, James A. Begg, Callum S. Xuan, Jinyi Johnson, Natalie T. Cole, Jason C. Kitching, Matthew O. JACS Au [Image: see text] Conglomerate crystallization is the spontaneous generation of individually enantioenriched crystals from a nonenantioenriched material. This behavior is responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The phenomenon of conglomerate crystallization of chiral organic molecules has been left largely undocumented, with no actively curated list available in the literature. While other crystallographic behaviors can be interrogated by automated searching, conglomerate crystallizations are not identified within the Cambridge Structural Database (CSD) and are therefore not accessible by conventional automated searching. By conducting a manual search of the CSD and literature, a list of over 1800 chiral species capable of conglomerate crystallization was curated by inspection of the racemic synthetic routes described in each publication. The majority of chiral conglomerate crystals are produced and published by synthetic chemists who seldom note and rarely exploit the implications this phenomenon can have on the enantiopurity of their crystalline materials. With their structures revealed, we propose that this list of compounds represents a new chiral pool which is not tied to biological sources of chirality. American Chemical Society 2022-09-23 /pmc/articles/PMC9597607/ /pubmed/36311827 http://dx.doi.org/10.1021/jacsau.2c00394 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Walsh, Mark P.
Barclay, James A.
Begg, Callum S.
Xuan, Jinyi
Johnson, Natalie T.
Cole, Jason C.
Kitching, Matthew O.
Identifying a Hidden Conglomerate Chiral Pool in the CSD
title Identifying a Hidden Conglomerate Chiral Pool in the CSD
title_full Identifying a Hidden Conglomerate Chiral Pool in the CSD
title_fullStr Identifying a Hidden Conglomerate Chiral Pool in the CSD
title_full_unstemmed Identifying a Hidden Conglomerate Chiral Pool in the CSD
title_short Identifying a Hidden Conglomerate Chiral Pool in the CSD
title_sort identifying a hidden conglomerate chiral pool in the csd
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9597607/
https://www.ncbi.nlm.nih.gov/pubmed/36311827
http://dx.doi.org/10.1021/jacsau.2c00394
work_keys_str_mv AT walshmarkp identifyingahiddenconglomeratechiralpoolinthecsd
AT barclayjamesa identifyingahiddenconglomeratechiralpoolinthecsd
AT beggcallums identifyingahiddenconglomeratechiralpoolinthecsd
AT xuanjinyi identifyingahiddenconglomeratechiralpoolinthecsd
AT johnsonnataliet identifyingahiddenconglomeratechiralpoolinthecsd
AT colejasonc identifyingahiddenconglomeratechiralpoolinthecsd
AT kitchingmatthewo identifyingahiddenconglomeratechiralpoolinthecsd