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Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process

Residual dipolar couplings (RDCs) offer additional information for structure elucidation by NMR spectroscopy. They are measured in anisotropic media, such as lyotropic liquid crystalline phases of polypeptides. Today, some suitable polypeptides are known. Nevertheless, structural influences of these...

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Autores principales: Alcaraz Janßen, Marcel, Thiele, Christina M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384199/
https://www.ncbi.nlm.nih.gov/pubmed/32134524
http://dx.doi.org/10.1002/chem.201905447
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author Alcaraz Janßen, Marcel
Thiele, Christina M.
author_facet Alcaraz Janßen, Marcel
Thiele, Christina M.
author_sort Alcaraz Janßen, Marcel
collection PubMed
description Residual dipolar couplings (RDCs) offer additional information for structure elucidation by NMR spectroscopy. They are measured in anisotropic media, such as lyotropic liquid crystalline phases of polypeptides. Today, some suitable polypeptides are known. Nevertheless, structural influences of these polypeptides on the alignment properties are not really understood. Thus, which influence a chiral side chain has on enantiodiscrimination and whether we can improve the enantiodifferentiation significantly by adding an additional chiral center in the side chain are questions of interest. Therefore, new diastereomeric polypeptide‐based alignment media with an additional chiral center in the side chain derived from perillyl alcohol were synthesized and their properties were investigated (secondary structure, liquid crystallinity, etc.). The enantiomers of isopinocampheol and β‐pinene were used as model analytes for the study of enantiodiscrimination. Additionally, the usage of (1)H–(1)H‐RDCs to improve the alignment tensor quality is demonstrated.
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spelling pubmed-73841992020-07-28 Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process Alcaraz Janßen, Marcel Thiele, Christina M. Chemistry Full Papers Residual dipolar couplings (RDCs) offer additional information for structure elucidation by NMR spectroscopy. They are measured in anisotropic media, such as lyotropic liquid crystalline phases of polypeptides. Today, some suitable polypeptides are known. Nevertheless, structural influences of these polypeptides on the alignment properties are not really understood. Thus, which influence a chiral side chain has on enantiodiscrimination and whether we can improve the enantiodifferentiation significantly by adding an additional chiral center in the side chain are questions of interest. Therefore, new diastereomeric polypeptide‐based alignment media with an additional chiral center in the side chain derived from perillyl alcohol were synthesized and their properties were investigated (secondary structure, liquid crystallinity, etc.). The enantiomers of isopinocampheol and β‐pinene were used as model analytes for the study of enantiodiscrimination. Additionally, the usage of (1)H–(1)H‐RDCs to improve the alignment tensor quality is demonstrated. John Wiley and Sons Inc. 2020-05-28 2020-06-23 /pmc/articles/PMC7384199/ /pubmed/32134524 http://dx.doi.org/10.1002/chem.201905447 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ 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 Full Papers
Alcaraz Janßen, Marcel
Thiele, Christina M.
Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process
title Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process
title_full Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process
title_fullStr Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process
title_full_unstemmed Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process
title_short Poly‐γ‐S‐perillyl‐l‐glutamate and Poly‐γ‐S‐perillyl‐d‐glutamate: Diastereomeric Alignment Media Used for the Investigation of the Alignment Process
title_sort poly‐γ‐s‐perillyl‐l‐glutamate and poly‐γ‐s‐perillyl‐d‐glutamate: diastereomeric alignment media used for the investigation of the alignment process
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384199/
https://www.ncbi.nlm.nih.gov/pubmed/32134524
http://dx.doi.org/10.1002/chem.201905447
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