Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess

Asymmetric amplification during self-replication is a key feature that is used to explain the origin of homochirality. Asymmetric autocatalysis of pyrimidyl alkanol in the asymmetric addition of diisopropylzinc to pyrimidine-5-carbaldehyde is a unique example of this phenomenon. Crystallization of z...

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Autores principales: Matsumoto, Arimasa, Abe, Takaaki, Hara, Atsushi, Tobita, Takayuki, Sasagawa, Taisuke, Kawasaki, Tsuneomi, Soai, Kenso
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4691336/
https://www.ncbi.nlm.nih.gov/pubmed/26494200
http://dx.doi.org/10.1002/anie.201508036
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author Matsumoto, Arimasa
Abe, Takaaki
Hara, Atsushi
Tobita, Takayuki
Sasagawa, Taisuke
Kawasaki, Tsuneomi
Soai, Kenso
author_facet Matsumoto, Arimasa
Abe, Takaaki
Hara, Atsushi
Tobita, Takayuki
Sasagawa, Taisuke
Kawasaki, Tsuneomi
Soai, Kenso
author_sort Matsumoto, Arimasa
collection PubMed
description Asymmetric amplification during self-replication is a key feature that is used to explain the origin of homochirality. Asymmetric autocatalysis of pyrimidyl alkanol in the asymmetric addition of diisopropylzinc to pyrimidine-5-carbaldehyde is a unique example of this phenomenon. Crystallization of zinc alkoxides of this 5-pyrimidyl alkanol and single-crystal X-ray diffraction analysis of the alkoxide crystals reveal the existence of tetramer or higher oligomer structures in this asymmetric autocatalytic system.
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spelling pubmed-46913362015-12-31 Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess Matsumoto, Arimasa Abe, Takaaki Hara, Atsushi Tobita, Takayuki Sasagawa, Taisuke Kawasaki, Tsuneomi Soai, Kenso Angew Chem Int Ed Engl Communications Asymmetric amplification during self-replication is a key feature that is used to explain the origin of homochirality. Asymmetric autocatalysis of pyrimidyl alkanol in the asymmetric addition of diisopropylzinc to pyrimidine-5-carbaldehyde is a unique example of this phenomenon. Crystallization of zinc alkoxides of this 5-pyrimidyl alkanol and single-crystal X-ray diffraction analysis of the alkoxide crystals reveal the existence of tetramer or higher oligomer structures in this asymmetric autocatalytic system. WILEY-VCH Verlag 2015-12-07 2015-10-23 /pmc/articles/PMC4691336/ /pubmed/26494200 http://dx.doi.org/10.1002/anie.201508036 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. https://creativecommons.org/licenses/by-nc-nd/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
spellingShingle Communications
Matsumoto, Arimasa
Abe, Takaaki
Hara, Atsushi
Tobita, Takayuki
Sasagawa, Taisuke
Kawasaki, Tsuneomi
Soai, Kenso
Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
title Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
title_full Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
title_fullStr Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
title_full_unstemmed Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
title_short Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
title_sort crystal structure of the isopropylzinc alkoxide of pyrimidyl alkanol: mechanistic insights for asymmetric autocatalysis with amplification of enantiomeric excess
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4691336/
https://www.ncbi.nlm.nih.gov/pubmed/26494200
http://dx.doi.org/10.1002/anie.201508036
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