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Pentapeptide Nanoreactor as a Platform for Halogenations, Diels–Alder Reaction, and Morita–Baylis–Hillman Reaction
[Image: see text] A pentapeptide nanoreactor has been designed and synthesized as a platform to carry out the traditional organic reactions such as bromination, iodination, cycloaddition, and condensation reactions. The pentapeptide Boc–Phe–Phe–Aib–Phe–Phe–OMe with a supramolecular helical structure...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714524/ https://www.ncbi.nlm.nih.gov/pubmed/31497704 http://dx.doi.org/10.1021/acsomega.9b01393 |
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author | Debnath, Mintu Sasmal, Supriya Podder, Debasish Haldar, Debasish |
author_facet | Debnath, Mintu Sasmal, Supriya Podder, Debasish Haldar, Debasish |
author_sort | Debnath, Mintu |
collection | PubMed |
description | [Image: see text] A pentapeptide nanoreactor has been designed and synthesized as a platform to carry out the traditional organic reactions such as bromination, iodination, cycloaddition, and condensation reactions. The pentapeptide Boc–Phe–Phe–Aib–Phe–Phe–OMe with a supramolecular helical structure and π-rich channel provides nanoconfinements and thus facilitates the organic reactions. Bromination and iodination of aniline take place without any halogen carrier (Lewis acid) in the pentapeptide platform. Iodination produced p-iodoaniline only. The Diels–Alder reaction between furan and maleic anhydride increased 2-fold in the pentapeptide platform and the Morita–Baylis–Hillman reaction of benzaldehyde and ethyl acrylate in methanol enhanced 1.5-fold. |
format | Online Article Text |
id | pubmed-6714524 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-67145242019-09-06 Pentapeptide Nanoreactor as a Platform for Halogenations, Diels–Alder Reaction, and Morita–Baylis–Hillman Reaction Debnath, Mintu Sasmal, Supriya Podder, Debasish Haldar, Debasish ACS Omega [Image: see text] A pentapeptide nanoreactor has been designed and synthesized as a platform to carry out the traditional organic reactions such as bromination, iodination, cycloaddition, and condensation reactions. The pentapeptide Boc–Phe–Phe–Aib–Phe–Phe–OMe with a supramolecular helical structure and π-rich channel provides nanoconfinements and thus facilitates the organic reactions. Bromination and iodination of aniline take place without any halogen carrier (Lewis acid) in the pentapeptide platform. Iodination produced p-iodoaniline only. The Diels–Alder reaction between furan and maleic anhydride increased 2-fold in the pentapeptide platform and the Morita–Baylis–Hillman reaction of benzaldehyde and ethyl acrylate in methanol enhanced 1.5-fold. American Chemical Society 2019-08-13 /pmc/articles/PMC6714524/ /pubmed/31497704 http://dx.doi.org/10.1021/acsomega.9b01393 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Debnath, Mintu Sasmal, Supriya Podder, Debasish Haldar, Debasish Pentapeptide Nanoreactor as a Platform for Halogenations, Diels–Alder Reaction, and Morita–Baylis–Hillman Reaction |
title | Pentapeptide Nanoreactor as a Platform for Halogenations,
Diels–Alder Reaction, and Morita–Baylis–Hillman
Reaction |
title_full | Pentapeptide Nanoreactor as a Platform for Halogenations,
Diels–Alder Reaction, and Morita–Baylis–Hillman
Reaction |
title_fullStr | Pentapeptide Nanoreactor as a Platform for Halogenations,
Diels–Alder Reaction, and Morita–Baylis–Hillman
Reaction |
title_full_unstemmed | Pentapeptide Nanoreactor as a Platform for Halogenations,
Diels–Alder Reaction, and Morita–Baylis–Hillman
Reaction |
title_short | Pentapeptide Nanoreactor as a Platform for Halogenations,
Diels–Alder Reaction, and Morita–Baylis–Hillman
Reaction |
title_sort | pentapeptide nanoreactor as a platform for halogenations,
diels–alder reaction, and morita–baylis–hillman
reaction |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714524/ https://www.ncbi.nlm.nih.gov/pubmed/31497704 http://dx.doi.org/10.1021/acsomega.9b01393 |
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